Water → 1,4,6-Trimethyl-2-oxo-1,2-dihydropyridine-3-carboxylic acid

HRID 2419958Notes

Reaction equation

HRID 2419958 reaction equation
[CH3:1][N:2]1[C:7]([CH3:8])=[CH:6][C:5]([CH3:9])=[C:4]([C:10]#N)[C:3]1=[O:12].S(=O)(=O)(O)[OH:14].[OH2:18]>>[CH3:1][N:2]1[C:7]([CH3:8])=[CH:6][C:5]([CH3:9])=[C:4]([C:10]([OH:14])=[O:18])[C:3]1=[O:12]

Participants

4

Reactant 3

HCID 962Water2×HCID 1118Sulfuric AcidHCID 46479Nicotinonitrile, 1,2-dihydro-2-oxo-1,4,6-trimethyl-

Product 1

HCID 65010061,4,6-Trimethyl-2-oxo-1,2-dihydropyridine-3-carboxylic acidYield 60%

Procedure

To a stirred mixture of 1-methyl-3-cyano-4,6-dimethylpyrid-2-one (144 g., 0.89 mole) and 110 ml. of water is slowly added concentrated sulfuric acid (220 ml.) and the solution is heated on a steam bath for 24 hours. The solution is poured into 6 liters of water, cooled, and the resulting precipitate is collected by filtration and dried in a vacuum oven to give 1-methyl-3-carboxy-4.6-dimethylpyrid-2-one, 97 g. (60% yield), mp. 200°-204° C.

Workup

  1. temperaturethe solution is heated on a steam bath for 24 hours
  2. temperaturecooled
  3. filtrationthe resulting precipitate is collected by filtration
  4. customdried in a vacuum oven

Sources & evidence

ORD record
ord-ee3814351d72449eb039a428e8e54c76
Source dataset
uspto-grants-1978_08
Patent number
US04108630

Reaction notes

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