3-Methylpyridine-4-carbonyl chloride

Base Information

• Chemical Name: 3-Methylpyridine-4-carbonyl chloride
• CAS No.: 64915-79-3
• Molecular Formula: C7H6 Cl N O
• Molecular Weight: 155.584
• Hs Code.: 2933399090
• DSSTox Substance ID: DTXSID30534767
• Wikidata: Q82408742
• Mol file: 64915-79-3.mol

Synonyms:64915-79-3;3-Methylpyridine-4-carbonyl chloride;3-METHYL-4-PYRIDINECARBONYL CHLORIDE;4-Pyridinecarbonyl chloride, 3-methyl- (9CI);4-Pyridinecarbonyl chloride, 3-methyl-;3-methyl-isonicotinoyl chloride;SCHEMBL1967163;DTXSID30534767;3-methylisonicotinic acid chloride;KSDVVNBPDOBZTI-UHFFFAOYSA-N;4-Pyridinecarbonyl chloride,3-methyl-(9ci)

Chemical Property of 3-Methylpyridine-4-carbonyl chloride

Chemical Property:

• PSA: 29.96000
• LogP: 1.76900
• XLogP3: 1.7
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 155.0137915
• Heavy Atom Count: 10
• Complexity: 138

Purity/Quality:

99% ^*data from raw suppliers

3-Methyl-4-pyridinecarbonylChloride ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=C(C=CN=C1)C(=O)Cl
• Uses: 3-Methyl-4-pyridinecarbonyl chloride is used as a reagent to synthesize azaindenoisoquinoline compounds, which have anticancer properties through the inhibition of topoisomerase I. 3-Methyl-4-pyridinecarbonyl chloride is also used as a reagent to prepare (1,2,4)Triazolo[4,3-a]quinoxaline derivatives, compounds that have phosphodiesterase inhibition properties in order to treat patients with CNS disorders.

Technology Process of 3-Methylpyridine-4-carbonyl chloride

There total 2 articles about 3-Methylpyridine-4-carbonyl chloride which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

3-methyl-isonicotinic acid (4021-12-9) → 5-methylpyridine-3-carbonyl chloride (64915-79-3)

Guidance literature:

With thionyl chloride; In dichloromethane; at 20 ℃; for 3h;

Reference yield:

3,4-Lutidin (583-58-4) → 5-methylpyridine-3-carbonyl chloride (64915-79-3)

Guidance literature:

Multi-step reaction with 2 steps

1: selenium(IV) oxide / diphenylether / 2 h / 150 - 180 °C

2: thionyl chloride / 3 h / Reflux

With selenium(IV) oxide; thionyl chloride; In diphenylether;

DOI:10.1021/jm201512x

Reference yield: 18.5%

5-methylpyridine-3-carbonyl chloride (64915-79-3) + 3-chloro-4-(1-ethyl-propoxy)-benzonitrile (1035216-83-1) → 3-[3-chloro-4-(1-ethyl-propoxy)-phenyl]-5-o-tolyl-[1,2,4]oxadiazole (1035212-21-5)

Guidance literature:

With pyridine; at 100 ℃;

upstream raw materials:

3-methyl-isonicotinic acid

3,4-Lutidin

Downstream raw materials:

3-[3-chloro-4-(1-ethyl-propoxy)-phenyl]-5-o-tolyl-[1,2,4]oxadiazole

N-(3-chlorophenyl)-N-((8-fluoro-2-oxo-1,2-dihydroquinolin-4-yl)methyl)-3-methylisonicotinamide

3-methyl-4-cyanopyridine

3-(bromomethyl)pyridine-4-carbonitrile

Refernces

• 1、 Honeycutt, Aaron P.,Hoover, Jessica M.. "Nickel-Catalyzed Oxidative Decarboxylative Annulation for the Synthesis of Heterocycle-Containing Phenanthridinones". supporting information. p. 7216 - 7219. Retrieved 2018/11/23.
• 2、 Steinhauer, Tamara N.,Girreser, Ulrich,Meier, Christopher,Cushman, Mark,Clement, Bernd. "One-Step Synthetic Access to Isosteric and Potent Anticancer Nitrogen Heterocycles with the Benzo[c]phenanthridine Scaffold". supporting information. p. 8301 - 8308. Retrieved 2016/06/13.