N-Methoxy-N-methylnicotinamide

Base Information

• Chemical Name: N-Methoxy-N-methylnicotinamide
• CAS No.: 95091-91-1
• Molecular Formula: C8H10N2O2
• Molecular Weight: 166.18
• Hs Code.: 2933399090
• European Community (EC) Number: 833-757-8
• DSSTox Substance ID: DTXSID50441666
• Nikkaji Number: J1.148.857I
• Wikidata: Q82258533
• Mol file: 95091-91-1.mol

Synonyms:N-METHOXY-N-METHYLNICOTINAMIDE;95091-91-1;n-methoxy-n-methylpyridine-3-carboxamide;3-Pyridinecarboxamide, N-methoxy-N-methyl-;SCHEMBL434252;N-methyl-N-methoxy-nicotinamide;DTXSID50441666;KFEZCMOHRDCFIQ-UHFFFAOYSA-N;VDA09191;MFCD11847417;AKOS008953236;SB53967;N-Methoxy-N-methyl-3-pyridinecarboxamide;AS-10408;CS-0044200;M3099;EN300-200428;Y10185;F1903-0200

Chemical Property of N-Methoxy-N-methylnicotinamide

Chemical Property:

• Refractive Index: 1.53
• Boiling Point: 317.3±15.0 °C(Predicted)
• PKA: 3.16±0.10(Predicted)
• PSA: 42.43000
• Density: 1.1
• LogP: 0.71500
• Storage Temp.: 2-8°C
• XLogP3: -0.4
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• Exact Mass: 166.074227566
• Heavy Atom Count: 12
• Complexity: 161

Purity/Quality:

NLT 98% ^*data from raw suppliers

N-methoxy-N-methylnicotinamide ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CN(C(=O)C1=CN=CC=C1)OC

Technology Process of N-Methoxy-N-methylnicotinamide

There total 10 articles about N-Methoxy-N-methylnicotinamide 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: 98.0%

nicotinic acid (59-67-6) + N,O-dimethylhydroxylamine*hydrochloride (6638-79-5) → N-methoxy-N-methylpyridine-3-carboxamide (95091-91-1)

Guidance literature:

With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; In acetonitrile; at 20 ℃; for 2h;

Reference yield: 95.0%

3-Bromopyridine (626-55-1,163928-56-1) + carbon monoxide (201230-82-2) + N,O-dimethylhydroxylamine*hydrochloride (6638-79-5) → N-methoxy-N-methylpyridine-3-carboxamide (95091-91-1)

Guidance literature:

With potassium carbonate; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; In toluene; at 105 ℃; for 12h; under 2250.23 Torr; Inert atmosphere; Green chemistry;

DOI:10.1039/c4ra04614e

Reference yield: 87.0%

3-pyridinecarbonyl chloride (10400-19-8) + N,O-dimethylhydroxylamine*hydrochloride (6638-79-5) → N-methoxy-N-methylpyridine-3-carboxamide (95091-91-1)

Guidance literature:

With N-ethyl-N,N-diisopropylamine; In dichloromethane;

DOI:10.1016/j.tetlet.2010.05.086

upstream raw materials:

3-pyridinecarbonyl chloride

N,O-dimethylhydroxylamine*hydrochloride

nicotinic acid

pyridine-3-carbonyl chloride hydrochloride

Downstream raw materials:

3-(1,3-dioxolan-2-yl)-1-(pyridin-3-yl)propan-1-one

rac-nornicotine

methyl-3-pyridylketone

Phenyl 6-ethyl-3-(N-methoxy-N-methylcarbomoyl)-1,2-dihydropyridinecarboxylate

Refernces

• 1、 Denisenko, Aleksandr,Garbuz, Pavel,Mykhailiuk, Pavel K.,Shishkina, Svetlana V.,Voloshchuk, Nataliya M.. "Saturated Bioisosteres of ortho-Substituted Benzenes". supporting information. p. 20515 - 20521. Retrieved 2020/08/21.
• 2、 Huang, Fei,Zhang, Songlin. "Iminyl Radicals by Reductive Cleavage of N-O Bond in Oxime Ether Promoted by SmI2: A Straightforward Synthesis of Five-Membered Cyclic Imines". supporting information. p. 7430 - 7434. Retrieved 2019/10/11.