Ammonia → 5-[4-(1H-imidazol-1-yl)phenyl]-6-methyl-2(1H)-pyridinone

HRID 364944Notes

Reaction equation

HRID 364944 reaction equation
[N:1]1([C:6]2[CH:11]=[CH:10][C:9]([C:12]3[CH:13]=[C:14](C#N)[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.S(=O)(=O)(O)O.N>>[N:1]1([C:6]2[CH:7]=[CH:8][C:9]([C:12]3[CH:13]=[CH:14][C:15](=[O:19])[NH:16][C:17]=3[CH3:18])=[CH:10][CH:11]=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 133942435-[4-(1H-imidazol-1-yl)phenyl]-6-methyl-2(1H)-pyridinoneYield 50.4%

Procedure

A solution of 1,2-dihydro-5-[4-(1H-imidazol-1-yl)phenyl]-6-methyl-2-oxo-3-pyridinecarbonitrile 21.8 g) in 110 ml of 85% (w/w) sulfuric acid is heated at 205° C. for 19 hours. The reaction mixture is cooled to room temperature, poured into 600 ml of ice, and the resulting solution adjusted to pH 8 with concentrated ammonia. The precipitate is collected and recrystallized from dimethylformamide to give 10.0 g of 5-[4-(1H-imidazol-1-yl)phenyl]-6-methyl-2(1H)-pyridinone, mp 310°-314° C.

Workup

  1. customThe precipitate is collected
  2. customrecrystallized from dimethylformamide

Sources & evidence

ORD record
ord-90058d4a19da491bbf9da5d4f06725b7
Source dataset
uspto-grants-1986_08
Patent number
US04607037

Reaction notes

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