Ammonia → 1,2-dihydro-5-[4-(1H-imidazol-1-yl)phenyl]-6-methyl-2-oxo-3-pyridinecarboxamide

Reaction equation

[N:1]1([C:6]2[CH:11]=[CH:10][C:9]([C:12]3[CH:13]=[C:14]([C:20]#[N:21])[C:15](=[O:19])[NH:16][C:17]=3[CH3:18])=[CH:8][CH:7]=2)[CH:5]=[CH:4][N:3]=[CH:2]1.N.S(=O)(=O)(O)[OH:24]>>[N:1]1([C:6]2[CH:11]=[CH:10][C:9]([C:12]3[CH:13]=[C:14]([C:20]([NH2:21])=[O:24])[C:15](=[O:19])[NH:16][C:17]=3[CH3:18])=[CH:8][CH:7]=2)[CH:5]=[CH:4][N:3]=[CH:2]1

Participants

Reactant 3

HCID 222Ammonia

HCID 1118Sulfuric Acid

HCID 104461365-(4-Imidazol-1-yl-phenyl)-6-methyl-2-oxo-1,2-dihydro-pyridine-3-carbonitrile

Product 1

HCID 133942441,2-dihydro-5-[4-(1H-imidazol-1-yl)phenyl]-6-methyl-2-oxo-3-pyridinecarboxamide

Procedure

A solution of 1,2-dihydro-5-[4-(1H-imidazol-1-yl)phenyl]-6-methyl-2-oxo-3-pyridinecarbonitrile (5.0 g) in 25 ml of concentrated sulfuric acid is heated on a steam bath for 40 minutes, cooled to room temperature and poured into 150 ml of ice. The mixture is adjusted to pH 8 with concentrated ammonia. The solid is collected and recrystallized successively from 10:1 water/acetic acid, dimethylformamide, and 2-methoxyethanol to give 2.06 g of 1,2-dihydro-5-[4-(1H-imidazol-1-yl)phenyl]-6-methyl-2-oxo-3-pyridinecarboxamide, mp 311°-315° C. (dec).