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

HRID 2164274Notes

Reaction equation

HRID 2164274 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

4

Reactant 3

HCID 222AmmoniaHCID 1118Sulfuric AcidHCID 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).

Workup

  1. customThe solid is collected
  2. customrecrystallized successively from 10:1 water/acetic acid, dimethylformamide, and 2-methoxyethanol

Sources & evidence

ORD record
ord-aaafe8a603de4f46a41233a69904c95c
Source dataset
uspto-grants-1985_03
Patent number
US04503061

Reaction notes

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