Nitric Acid → 4-Hydroxy-6-methyl-3-nitropyridin-2(1H)-one

HRID 1690213Notes

Reaction equation

HRID 1690213 reaction equation
[N+:1]([O-:4])(O)=[O:2].[OH:5][C:6]1[CH:11]=[C:10]([CH3:12])[NH:9][C:8](=[O:13])[CH:7]=1>>[OH:5][C:6]1[CH:11]=[C:10]([CH3:12])[NH:9][C:8](=[O:13])[C:7]=1[N+:1]([O-:4])=[O:2]

Participants

3

Reactant 2

HCID 944Nitric AcidHCID 546914196-Methylpyridine-2,4-diol

Product 1

HCID 546856194-Hydroxy-6-methyl-3-nitropyridin-2(1H)-oneYield 80%

Procedure

To 70% nitric acid (30 mL), 4-hydroxy-6-methylpyridin-2(1H)-one (10.5 g, 83.9 mmol) was added under ice-cold conditions, and the resultant mixture was stirred at 70° C. for 1.5 hours. The reaction solution was added to ice water (70 mL) under ice-cold conditions. The reaction solution was filtered, washed sequentially with cold water, tetrahydrofuran and diethylether, and then dried. 4-Hydroxy-6-methyl-3-nitropyridin-2(1H)-one (11.5 g, yield 80%) was obtained as a yellow crystal.

Workup

  1. filtrationThe reaction solution was filtered
  2. washwashed sequentially with cold water, tetrahydrofuran and diethylether
  3. customdried

Sources & evidence

ORD record
ord-79829a90a19e432aa2be0be2c511820e
Source dataset
uspto-grants-2012_04
Patent number
US08153634B2

Reaction notes

Loading…