53014-84-9

Basic information

• Product Name: 3-FORMYL-6-METHYL-PYRIDINE
• Synonyms: 6-METHYL-3-PYRIDINECARBOXALDEHYDE;5-FORMYL-2-PICOLINE;3-FORMYL-6-METHYL-PYRIDINE;6-Methylpyridine-3-carboxaldehyde;6-Methylnicotinaldehyde;5-Formyl-2-methylpyridine;3-Formyl-6-methyl-pyridine ,97%;3-Pyridinecarboxaldehyde, 6-methyl-
• CAS NO: 53014-84-9
• Molecular Formula: C₇H₇NO
• Molecular Weight: 121.14
• Product Categories: Pyridine;Pyridines;Building Blocks;Aldehydes;C7;C7 to C8;Carbonyl Compounds;Chemical Synthesis;Heterocyclic Building Blocks;Organic Building Blocks;Heterocycle-Pyridine series
• Mol File: 53014-84-9.mol
• Article Data: 28

Chemical Properties

• Boiling Point: 95℃/20mm
• Flash Point: 88℃
• Appearance: /Liquid
• Density: 1.084
• Vapor Pressure: 0.162mmHg at 25°C
• Refractive Index: 1.546
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• PKA: 4.15±0.10(Predicted)
• Sensitive: Moisture Sensitive
• CAS DataBase Reference: 3-FORMYL-6-METHYL-PYRIDINE(CAS DataBase Reference)
• NIST Chemistry Reference: 3-FORMYL-6-METHYL-PYRIDINE(53014-84-9)
• EPA Substance Registry System: 3-FORMYL-6-METHYL-PYRIDINE(53014-84-9)

Safety Data

• Hazard Codes: Xn
• Statements: 22-36
• Safety Statements: 26
• WGK Germany: 3
• Hazardous Substances Data: 53014-84-9(Hazardous Substances Data)

Usage

General Description

3-Formyl-6-methyl-pyridine is a chemical compound with the molecular formula C7H7NO. It is a derivative of pyridine, an aromatic heterocyclic compound. This chemical is commonly used as a building block in the synthesis of pharmaceuticals and agricultural chemicals. It has a strong odor and is a volatile liquid at room temperature. The compound is also used as a flavoring agent in food products and as an intermediate in the production of dyes and other organic compounds. It is important to handle this chemical with care, as it can be harmful if ingested or inhaled and can cause irritation to the skin and eyes.

InChI:InChI=1/C7H7NO/c1-6-2-3-7(5-9)4-8-6/h2-5H,1H3

Synthetic route

6-methyl-3-pyridinemethanol (34107-46-5) → 2-methyl-5-formylpyridine (53014-84-9)

Conditions	Yield
Stage #1: 6-methyl-3-pyridinemethanol With oxalyl dichloride; dimethyl sulfoxide In dichloromethane at -60℃; for 1.33333h; Stage #2: With triethylamine In dichloromethane at -60 - 20℃; for 0.166667h;	85%
With oxalyl dichloride; dimethyl sulfoxide; triethylamine In dichloromethane at -60℃; for 1.5h;	85%
With lead(IV) acetate In toluene for 2.5h; Heating;	57%

5-bromo-2-methylpyridine (3430-13-5) + N,N-dimethyl-formamide (68-12-2, 33513-42-7) → 2-methyl-5-formylpyridine (53014-84-9)

Conditions	Yield
Stage #1: 5-bromo-2-methylpyridine With n-butyllithium; isopropylmagnesium chloride In tetrahydrofuran; hexane at -10℃; for 0.5h; Stage #2: N,N-dimethyl-formamide In tetrahydrofuran at 0℃; for 2h;	85%
Stage #1: 5-bromo-2-methylpyridine With n-butyllithium In tetrahydrofuran at -78℃; for 1h; Stage #2: N,N-dimethyl-formamide In tetrahydrofuran at -78℃; for 1h;	72%
Stage #1: 5-bromo-2-methylpyridine With n-butyllithium In tetrahydrofuran at -78℃; for 1h; Stage #2: N,N-dimethyl-formamide In tetrahydrofuran at -78℃; for 1h;	72%
Stage #1: 5-bromo-2-methylpyridine With n-butyllithium; isopropylmagnesium chloride In tetrahydrofuran; hexane at 10℃; for 1h; Stage #2: N,N-dimethyl-formamide In tetrahydrofuran; hexane at 20℃; for 2h;	38%
Stage #1: 5-bromo-2-methylpyridine With isopropylmagnesium chloride In tetrahydrofuran at 0 - 20℃; for 6h; Stage #2: N,N-dimethyl-formamide In tetrahydrofuran at 0 - 20℃;	4.5 g

dihydroxy-methyl-borane (13061-96-6) + 6-bromonicotinaldehyde (149806-06-4) → 2-methyl-5-formylpyridine (53014-84-9)

Conditions	Yield
	16%

6-methyl-pyridine-3-carbaldehyde semicarbazone (106837-80-3) → 2-methyl-5-formylpyridine (53014-84-9)

Conditions	Yield
With hydrogenchloride; water; 3-nitro-benzaldehyde

2,5-dimethylpyridine (589-93-5) → 5-methylpicolinaldehyde (4985-92-6) + 2-methyl-5-formylpyridine (53014-84-9) + carbon oxides

Conditions	Yield
β-VO(PO3)2 In gas at 400℃; Product distribution; Rate constant; selectivity of reaction, rates of partial and total oxidation;

N-methoxy-N-methyl-6-methylnicotinamide (221615-71-0) → 2-methyl-5-formylpyridine (53014-84-9) + C5H5NCH2C(NC2H6O)2

Conditions	Yield
With diisobutylaluminium hydride In toluene at -20 - -5℃; for 0.5h;

Methyl 6-methylnicotinate (5470-70-2) → 2-methyl-5-formylpyridine (53014-84-9)

Conditions	Yield
Multi-step reaction with 2 steps 1: i-PrMgCl / toluene; tetrahydrofuran / 0.5 h / -10 °C 2: DIBAL-H / toluene / 0.5 h / -20 - -5 °C View Scheme
Multi-step reaction with 2 steps 1: 75 percent / LAH / diethyl ether / 0.5 h / -78 °C 2: 1.) oxalyl chloride, dimethyl sulfoxide, 2.) triethylamine / 1.) methylene chloride, -60 deg C, 20 min, 2.) from -60 deg C to RT View Scheme
Stage #1: Methyl 6-methylnicotinate With lithium aluminium tetrahydride In tetrahydrofuran at -78℃; for 4h; Stage #2: With manganese(IV) oxide In dichloromethane for 6h; Heating / reflux;

ethyl 6-methylnicotinate (21684-59-3) → 2-methyl-5-formylpyridine (53014-84-9)

Conditions	Yield
Multi-step reaction with 2 steps 1: 89 percent / sodium bis(2-methoxyethoxy)aluminum hydride / diethyl ether / Heating 2: 57 percent / Pb(OAc)4 / toluene / 2.5 h / Heating View Scheme
Multi-step reaction with 2 steps 1: lithium aluminium tetrahydride / tetrahydrofuran View Scheme
Multi-step reaction with 2 steps 1: diethyl ether; water 2: pyridine; water View Scheme

6-methylnicotinonitrile (3222-48-8) → 2-methyl-5-formylpyridine (53014-84-9)

Conditions	Yield
Multi-step reaction with 2 steps 1: Raney nickel; ethanol / Hydrogenation.unter Zusatz einer wss. Loesung von Semicarbazid-hydrochlorid und Natriumacetat 2: 3-nitro-benzaldehyde; hydrochloric acid; water View Scheme

2-methyl-5-vinylpyridine (140-76-1) → 2-methyl-5-formylpyridine (53014-84-9)

Conditions	Yield
With sodium periodate; osmium(VIII) oxide In 1,2-dimethoxyethane; water

N-methoxy-N-methyl-6-methylnicotinamide (221615-71-0) → 2-methyl-5-formylpyridine (53014-84-9)

Conditions	Yield
Stage #1: N-methoxy-N-methyl-6-methylnicotinamide With diisobutylaluminium hydride In hexane; dichloromethane at -10℃; for 0.166667h; Inert atmosphere; Stage #2: With water In hexane; dichloromethane at 20℃; for 1h;

6-methylnicotinic acid (3222-47-7) → 2-methyl-5-formylpyridine (53014-84-9)

Conditions	Yield
Swern Oxidation;

2-methyl-5-formylpyridine (53014-84-9) → (3E)-6-methylpyridine-3-carbaldehyde oxime

Conditions	Yield
With hydroxylamine In methanol; water at 20 - 40℃; for 23h; Inert atmosphere;	98%

2-methyl-5-formylpyridine (53014-84-9) → 6-methylnicotinaldehyde oxime (89693-75-4)

Conditions	Yield
With hydroxylamine In methanol; water at 20 - 40℃; for 4h;	94%
With hydroxylamine In methanol; water at 40℃; for 2h;	94%
With hydroxylamine hydrochloride; sodium carbonate In ethanol; water at 20℃;

2-methyl-5-formylpyridine (53014-84-9) + allylmagnesium bromide (1730-25-2) → 1-(6-methylpyridin-3-yl)but-3-en-1-ol (1566970-97-5)

Conditions	Yield
In tetrahydrofuran at -40 - -20℃; for 0.166667h;	94%

2-methyl-5-formylpyridine (53014-84-9) + (±)-3,7-dimethyloctanehydrazide → 3,7-dimethyl-N'-[(6-methylpyridin-3-yl)methylidene]octanehydrazide

Conditions	Yield
In methanol Reflux;	92%

2-methyl-5-formylpyridine (53014-84-9) + 6‑(1H‑indol‑3‑yl)‑4,5′‑bipyrimidine‑2‑amine → (E)‑N‑[6‑(1H‑indol‑3‑yl)‑4,5′‑bipyrimidine‑2‑yl]‑1‑(6‑methylpyridin‑3‑yl)methanimine

Conditions	Yield
With acetic acid In ethanol for 18h; Reflux;	90%

2-methyl-5-formylpyridine (53014-84-9) + malonic acid dimethyl ester (108-59-8) → dimethyl 2-((6-methylpyridin-3-yl)methylene)malonate

Conditions	Yield
With piperidine; acetic acid In toluene at 110℃; for 18h; Schlenk technique; Inert atmosphere; Sealed tube;	87%

2-methyl-5-formylpyridine (53014-84-9) + malonic acid (141-82-2) → 3-(6-methyl-pyridin-3-yl)-acrylic acid (117830-17-8)

Conditions	Yield
With piperidine In pyridine at 100℃;	77%

2-methyl-5-formylpyridine (53014-84-9) + uracil (66-22-8) → 5-<(6-methyl-3-pyridinyl)hydroxymethyl>-2,4(1H,3H)-pyrimidinedione (83902-97-0) + 5,5'-<(6-methyl-3-pyridinyl)methylene>bis(2,4(1H,3H)-pyrimidinedione) (102396-65-6)

Conditions	Yield
With hydrogenchloride for 8h; Heating;	A 70% B n/a

2-methyl-5-formylpyridine (53014-84-9) + ethyl 2-cyanoacetate (105-56-6) → ethyl (2E)-2-cyano-3-(6-methylpyridin-3-yl)prop-2-enoate

Conditions	Yield
With piperidine; acetic acid In ethanol at 20℃; for 16h;	70%

2-methyl-5-formylpyridine (53014-84-9) + ethyl acrylate (140-88-5) → 2-[(hydroxy)(6-methylpyridin-3-yl)methyl] acrylic acid ethyl ester (1362851-35-1)

Conditions	Yield
With 1,4-diaza-bicyclo[2.2.2]octane at 20℃;	62%

2-methyl-5-formylpyridine (53014-84-9) + malonic acid (141-82-2) → 3-amino-3-(6-methyl-3-pyridyl)propionic acid (252989-81-4)

Conditions	Yield
With ammonium acetate In ethanol for 6h; Condensation; Heating;	61%
With ammonium acetate In ethanol Reflux;

2-methyl-5-formylpyridine (53014-84-9) + N-{3-[4-amino-1-hydroxy-4-(3,3-dimethylbutyl)-3-oxo-3,4-dihydronaphthalen-2-yl]-1,1-dioxido-4H-1,2,4-benzothiadiazin-7-yl}methanesulfonamide hydrochloride (909106-48-5) → N-[3-(4-(3,3-dimethylbutyl)-1-hydroxy-4-{[(6-methylpyridin-3-yl)methyl]amino}-3-oxo-3,4-dihydronaphthalen-2-yl)-1,1-dioxido-4H-1,2,4-benzothiadiazin-7-yl]methanesulfonamide

Conditions

Yield

Stage #1: N-{3-[4-amino-1-hydroxy-4-(3,3-dimethylbutyl)-3-oxo-3,4-dihydronaphthalen-2-yl]-1,1-dioxido-4H-1,2,4-benzothiadiazin-7-yl}methanesulfonamide hydrochloride With N-ethyl-N,N-diisopropylamine In 1,2-dichloro-ethane at 20℃; for 0.0833333h; Stage #2: 2-methyl-5-formylpyridine With magnesium sulfate In 1,2-dichloro-ethane at 50℃; for 18h; Stage #3: With sodium tris(acetoxy)borohydride; acetic acid In 1,2-dichloro-ethane at 20℃; for 18h;

58%

2-methyl-5-formylpyridine (53014-84-9) + (bromomethyl)triphenyl phosphonium bromide (1034-49-7) → 5-(2-bromovinyl)-2-methylpyridine (1189785-37-2)

Conditions	Yield
Stage #1: (bromomethyl)triphenyl phosphonium bromide With potassium tert-butylate In tetrahydrofuran at -78 - 0℃; Inert atmosphere; Stage #2: 2-methyl-5-formylpyridine In tetrahydrofuran at -78℃; for 5h;	56%

2-methyl-5-formylpyridine (53014-84-9) + 1-(7-hydroxy-2-methyl-2-(4-methylpent-3-en-1-yl)-2H-chromen-8-yl)ethan-1-one (54246-37-6) → (E)-1-(7-hydroxy-2-methyl-2-(4-methylpent-3-en-1-yl)-2H-chromen-8-yl)-3-(6-methylpyridin-3-yl)prop-2-en-1-one

Conditions	Yield
Stage #1: 1-(7-hydroxy-2-methyl-2-(4-methylpent-3-en-1-yl)-2H-chromen-8-yl)ethan-1-one With sodium hydride In tetrahydrofuran at 0 - 20℃; Stage #2: 2-methyl-5-formylpyridine In tetrahydrofuran at 0 - 30℃;	55%

2-methyl-5-formylpyridine (53014-84-9) + 2-(furan-2-yl)cyclopropanecarbohydrazide → (E)-2-(furan-2-yl)-N'-((6-methylpyridin-3-yl)methylene)cyclopropanecarbohydrazide

Conditions	Yield
With zinc(II) oxide In ethanol at 20℃; Reagent/catalyst; Solvent; Green chemistry;	51%

2-methyl-5-formylpyridine (53014-84-9) + sodium chlorodifluoroacetate (1895-39-2) → 5-(2,2-difluorovinyl)-2-methylpyridine

Conditions	Yield
With triphenylphosphine In N,N-dimethyl-formamide at 100℃; Inert atmosphere;	46%

2-methyl-5-formylpyridine (53014-84-9) + isopropylmagnesium chloride (1068-55-9) → 1-(6-methylpyridin-3-yl)-2-methylpropan-1-ol

Conditions	Yield
With diisopropyl zinc; (2S)-(−)-3-exo-(morpholino)isoborneol In tetrahydrofuran; diethyl ether at 20℃; for 1h; Inert atmosphere; Schlenk technique;	39%
In tetrahydrofuran Inert atmosphere;

2-methyl-5-formylpyridine (53014-84-9) + 2-(4-(piperazin-1-yl)phenyl)benzo[d]oxazole (885275-02-5) → 2-(4-(4-((6-methylpyridin-3-yl)methyl)piperazin-1-yl)phenyl)benzo[d]oxazole (1426259-87-1)

Conditions	Yield
With formic acid In N,N-dimethyl-formamide at 100℃; for 3h; Inert atmosphere;	38%

2-methyl-5-formylpyridine (53014-84-9) + 4-[(4-{5-[(piperidin-4-yl)methoxy]pyridine-2-carbonyl}-piperazin-1-yl)methyl]benzonitrile → 4-({4-[5-({1-[(6-methylpyridin-3-yl)methyl]piperidin-4-yl}methoxy)pyridine-2-carbonyl]piperazin-1-yl}methyl)-benzonitrile tetrahydrochloride

Conditions	Yield
Stage #1: 2-methyl-5-formylpyridine; 4-[(4-{5-[(piperidin-4-yl)methoxy]pyridine-2-carbonyl}-piperazin-1-yl)methyl]benzonitrile With sodium tris(acetoxy)borohydride; acetic acid In dichloromethane at 20℃; Stage #2: With hydrogenchloride In 1,4-dioxane; methanol	38%

2-methyl-5-formylpyridine (53014-84-9) + (Z)-5-((2-(4-(aminomethyl)piperidin-1-yl)pyrimidin-4-yl)methylene)thiazolidine-2,4-dione (1312662-54-6) + trifluoroacetic acid (76-05-1) → (Z)-5-((2-(4-((((6-methylpyridin-3-yl)methyl)amino)methyl)piperidin-1-yl)pyrimidin-4-yl)methylene)thiazolidine-2,4-dione trifluoroacetate

Conditions

Yield

Stage #1: 2-methyl-5-formylpyridine; (Z)-5-((2-(4-(aminomethyl)piperidin-1-yl)pyrimidin-4-yl)methylene)thiazolidine-2,4-dione With N-ethyl-N,N-diisopropylamine In cis-1,2-Dichloroethylene; N,N-dimethyl-formamide at 20℃; for 1h; Stage #2: With sodium tris(acetoxy)borohydride In cis-1,2-Dichloroethylene; N,N-dimethyl-formamide at 20℃; for 16h; Stage #3: trifluoroacetic acid In cis-1,2-Dichloroethylene for 24h;

37.2%

2-methyl-5-formylpyridine (53014-84-9) + C27H31N7O3 → C29H30N8O

Conditions	Yield
Stage #1: C27H31N7O3 With trifluoroacetic acid In dichloromethane at 20℃; for 3h; Stage #2: 2-methyl-5-formylpyridine With acetic acid at 20℃; for 0.5h; Stage #3: With sodium tris(acetoxy)borohydride at 20℃;	36%

2-methyl-5-formylpyridine (53014-84-9) + 2-{[4-tert-butyl-5-(1H-1,2,4-triazol-1-yl)-1,3-thiazol-2-yl]imino}-1,3-thiazolidin-4-one → 2-{(4-tert-butyl-5-(1H-1,2,4-triazol-1-yl)thiazole-2-yl)imino}-5-[(6-methylpyridin-3-yl)methylidene]-4-thiazolidinone

Conditions	Yield
With sodium acetate; acetic acid for 10h; Reflux;	33%

2-methyl-5-formylpyridine (53014-84-9) + 4,5-diamino-6-chloro-N4-methylpyrimidine (52602-68-3) → 6-chloro-9-methyl-8-(6-methylpyridin-3-yl)-9H-purine

Conditions	Yield
With iron(III) chloride hexahydrate In N,N-dimethyl-formamide at 90℃; for 16h;	33%

2-methyl-5-formylpyridine (53014-84-9) + diethylamine (109-89-7) → N-ethyl-N-((6-methylpyridin-3-yl)methyl)ethanamine

Conditions	Yield
With sodium tris(acetoxy)borohydride In 1,2-dichloro-ethane for 16h;	31%

2-methyl-5-formylpyridine (53014-84-9) + (-)-2-((3,4-trans)-4-methylpyrrolidin-3-yl)-7-(tetrahydro-2H-pyran-4-yl)imidazo[5,1-f][1,2,4]triazin-4(3H)-one → (+)-2-((3,4-trans)-4-methyl-1-((6-methylpyridin-3-yl)methyl)pyrrolidin-3-yl)-7-(tetrahydro-2H-pyran-4-yl)imidazo[5,1-f][1,2,4]triazin-4(3H)-one

Conditions	Yield
Stage #1: 2-methyl-5-formylpyridine; (-)-2-((3,4-trans)-4-methylpyrrolidin-3-yl)-7-(tetrahydro-2H-pyran-4-yl)imidazo[5,1-f][1,2,4]triazin-4(3H)-one With methanol at 20℃; for 2h; Inert atmosphere; Stage #2: With sodium cyanoborohydride at 20℃; for 8h; Inert atmosphere;	21%

2-methyl-5-formylpyridine (53014-84-9) + 2-amino-N-(4-(methylthio)phenyl)benzamide → 2-(6-methylpyridin-3-yl)-3-(4-(methylthio)phenyl)quinazolin-4(3H)-one (1235480-42-8)

Conditions	Yield
With copper dichloride In ethanol for 6h; Reflux;	19%

2-methyl-5-formylpyridine (53014-84-9) + 2-amino-N-(4-cyclopropylphenyl)benzamide (1235480-97-3) → 3-(4-cyclopropylphenyl)-2-(6-methylpyridin-3-yl)quinazolin-4(3H)-one (1235480-46-2)

Conditions	Yield
With copper dichloride In ethanol for 2.5h; Reflux;	15%

Upstream product

• 3430-13-5 5-bromo-2-methylpyridine 
• 68-12-2 N,N-dimethyl-formamide 
• 140-76-1 2-methyl-5-vinylpyridine 
• 221615-71-0 N-methoxy-N-methyl-6-methylnicotinamide 
• 589-93-5 2,5-dimethylpyridine 
• 34107-46-5 6-methyl-3-pyridinemethanol 
• 106837-80-3 6-methyl-pyridine-3-carbaldehyde semicarbazone 
• 3222-47-7 6-methylnicotinic acid 
• 3222-48-8 6-methylnicotinonitrile 
• 21684-59-3 ethyl 6-methylnicotinate 
• 5470-70-2 Methyl 6-methylnicotinate 
• 13061-96-6 dihydroxy-methyl-borane 
• 149806-06-4 6-bromonicotinaldehyde 

Downstream Products

• 90196-84-2 2-Methyl-5-<2-amino-ethyl>-pyridin 
• 1428969-86-1 1-(1H-indol-3-yl)-2-((3-methoxyphenyl)amino)-2-(6-methylpyridin-3-yl)ethanone 
• 1428973-15-2 3-methoxy-N-((6-methylpyridin-3-yl)methylene)aniline 
• 1426259-87-1 2-(4-(4-((6-methylpyridin-3-yl)methyl)piperazin-1-yl)phenyl)benzo[d]oxazole 
• 1417700-05-0 C₂₇H₃₃N₃O₃ 
• 1424330-36-8 C₂₂H₂₄Cl₂N₄O₂ 
• 1366232-75-8 C₂₂H₂₂N₄O 

Relevant articles and documents

Bromine-magnesium exchange of 5-bromo-2-picoline via an organomagnesium complex nBu2iPrMgLi: A new preparation methodology of functionalized picolines under noncryogenic conditions

The organomagnesium complex nBu2iPrMgLi, readily prepared from nBuLi and iPrMgCl (2:1), is quite efficient for the bromine-magnesium exchange of 5-bromo-2-picoline under noncryogenic conditions (at -10°C). The resulting picolylmagnesium complex reacts with various electrophiles to afford functionalized picolines.

2 - methyl - 5 - vinyl pyridine synthesis method (by machine translation)

The invention discloses a 2 - methyl - 5 - vinyl pyridine synthesis method, for the purpose of, reduce the synthesis step, to simplify the processing process, and improving the yield and save the cost, reducing chemical raw material consumption, effective protection of the environment, the use of the technical proposal is: (1) the raw material 6 - methyl nicotinic acid methyl ester is reduced to the 2 - methyl - 5 - pyridine base formaldehyde; (2) preparing the phosphorus ylide reagent; (3) the 2 - methyl - 5 - pyridyl formaldehyde and phosphorus ylide reagent in the reaction of 2 - methyl - 5 - vinyl pyridine, concentrated rectification to obtain the product. (by machine translation)

KYNURENINE PRODUCTION INHIBITOR

Provided is a kynurenine production inhibitor comprising a nitrogen-containing heterocyclic compound represented by formula (I): (wherein R50 and R51 may be the same or different and each represent a hydrogen atom or the like, G1 and G2 may be the same or different and each represent a nitrogen atom or the like, X represents formula (III): (wherein m1 and m2 may be the same or different and each represent an integer of 0 or 1, Y represents an oxygen atom or the like, and R6 and R7 may be the same or different and each represent a hydrogen atom or the like), R1 represents optionally substituted lower alkyl or the like, R2 represents a hydrogen atom or the like, and R3 represents optionally substituted lower alkyl or the like), and the like.