Acetic Anhydride → N-(4-methyl-5-nitropyridin-2-yl)acetamide

Reaction equation

[CH3:1][C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][N:5]=[C:4]([NH2:11])[CH:3]=1.[C:12](OC(=O)C)(=[O:14])[CH3:13]>>[CH3:1][C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][N:5]=[C:4]([NH:11][C:12](=[O:14])[CH3:13])[CH:3]=1

Participants

Reactant 2

HCID 7918Acetic Anhydride

HCID 2431652-Amino-4-methyl-5-nitropyridine

Product 1

HCID 13567013N-(4-methyl-5-nitropyridin-2-yl)acetamideYield 87%

Conditions

Temperature: 90 °C

Procedure

A mixture of 4-methyl-5-nitropyridin-2-amine (5 g, 32 mmol) and acetic anhydride (20 mL) was heated at 90° C. for 4 hours. After cooling the solvent was evaporated under vacuum. The concentrated mass was dissolved in toluene and evaporated under vacuum. The resulting solid was triturated with diethyl ether and filtered to afford N-(4-methyl-5-nitropyridin-2-yl) acetamide (5.5 g, 87%).

Workup

temperatureAfter cooling the solvent
customwas evaporated under vacuum
dissolutionThe concentrated mass was dissolved in toluene
customevaporated under vacuum
customThe resulting solid was triturated with diethyl ether
filtrationfiltered

Sources & evidence

ORD record: ord-d06bd54f5f924e2ebe9150a2b1d7623e
Source dataset: uspto-grants-2015_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08980911B2

Reaction notes

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