Oxoamide

Base Information

• Chemical Name: Oxoamide
• CAS No.: 713-05-3
• Molecular Formula: C₁₀H₁₂N₂O₂
• Molecular Weight: 192.217
• Hs Code.: 2933399090
• UNII: OL86R2ULD8
• DSSTox Substance ID: DTXSID80862385
• Nikkaji Number: J557.309B
• Metabolomics Workbench ID: 37542
• ChEMBL ID: CHEMBL3544600
• Mol file: 713-05-3.mol

Synonyms:gamma-(3-pyridyl)-gamma-oxo-N-methylbutyramide;oxoamide

Chemical Property of Oxoamide

Chemical Property:

• Vapor Pressure: 3.16E-08mmHg at 25°C
• Melting Point: 117-120°C
• Boiling Point: 448.2°C at 760 mmHg
• Flash Point: 224.9°C
• PSA: 59.06000
• Density: 1.133g/cm³
• LogP: 1.18140
• Storage Temp.: -20°C Freezer
• XLogP3: -0.3
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 4
• Exact Mass: 192.089877630
• Heavy Atom Count: 14
• Complexity: 216

Purity/Quality:

99% ^*data from raw suppliers

N-METHYL- -OXO-3-PYRIDINEBUTANAMIDE 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CNC(=O)CCC(=O)C1=CN=CC=C1
• Uses: An metabolite of Cotinine. In equilibrium with 5?Hydroxycotinine the cyclized form

Technology Process of Oxoamide

There total 8 articles about Oxoamide 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: 70.0%

4-oxo-4-(pyridin-3-yl)butanoic acid (4192-31-8) + methylamine hydrochloride (593-51-1) → 4-(3-pyridyl)-4-oxo-N-methylbutyramide (713-05-3) + 5-hydroxy-1-methyl-5-(3-pyridyl)-2-pyrrolidinone (61192-50-5,75919-05-0)

Guidance literature:

With 1-hydroxy-pyrrolidine-2,5-dione; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; N-ethyl-N,N-diisopropylamine; In dimethyl sulfoxide; at 20 ℃; for 22h;

DOI:10.1021/acs.chemrestox.6b00384

Reference yield: 15.0%

5-hydroxy-1-methyl-5-(3-pyridyl)-2-pyrrolidinone (61192-50-5,75919-05-0) → 4-(3-pyridyl)-4-oxo-N-methylbutyramide (713-05-3)

Guidance literature:

In water;

DOI:10.1021/jo00317a021

Reference yield:

(S)-3,3-dibromocotinine (74093-56-4) → 4-(3-pyridyl)-4-oxo-N-methylbutyramide (713-05-3)

Guidance literature:

Multi-step reaction with 4 steps

1: 90 percent / KOH / -10 deg C, then 2 h room temperature

2: 82 percent / 15 percent aqueous HBr / 2 h / 95 °C

3: 92 percent / H₂ / 10percent Pd/C / ethyl acetate / 20 h

4: 15 percent / H₂O

With potassium hydroxide; hydrogen bromide; hydrogen; palladium on activated charcoal; In water; ethyl acetate;

DOI:10.1021/jo00317a021

upstream raw materials:

5-hydroxy-1-methyl-5-(3-pyridyl)-2-pyrrolidinone

(S)-3,3-dibromocotinine

5-hydroxy-1-methyl-5-(3-pyridinyl)-3-pyrrolin-2-one

(R,S)-1-methyl-5-(3'-pyridyl)-5-methoxypyrrolin-2-one

Refernces

• 1、 Carlson, Erik S.,Upadhyaya, Pramod,Hecht, Stephen S.. "Evaluation of Nitrosamide Formation in the Cytochrome P450-Mediated Metabolism of Tobacco-Specific Nitrosamines". . p. 2194 - 2205. Retrieved 2016/12/26.