Water → HCID 20312182, compound

Reaction equation

[CH2:1]([N:11]1[C:16]([CH3:17])=[CH:15][C:14]([CH3:18])=[C:13]([C:19]#N)[C:12]1=[O:21])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH3:10].[OH2:22].S(=O)(=O)(O)[OH:24]>>[CH2:1]([N:11]1[C:16]([CH3:17])=[CH:15][C:14]([CH3:18])=[C:13]([C:19]([OH:24])=[O:22])[C:12]1=[O:21])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH3:10]

Participants

Reactant 3

HCID 962Water

HCID 1118Sulfuric Acid

HCID 20312200HCID 20312200, compound

Product 1

HCID 20312182HCID 20312182, compound

Procedure

1-(n-decyl)-3-cyano-4,6-dimethylpyrid-2-one (94.6 g., 0.33 mole) is dissolved in concentrated sulfuric acid (300 ml.) and crushed ice (90 g.) is slowly added while maintaining the reaction temperature below 75° C. The reaction mixture is then heated on a steam bath for 23 hours. The cooled reaction mixture is poured onto ice (700 g.) and the reaction mixture is diluted to 2300 ml. with water. The solid is collected by filtration and then triturated with dilute sodium hydroxide and filtered. The alkaline filtrate is acidified to pH 1 with concentrated hydrochloric acid. The resulting solid is collected by filtration and vacuum dried to give 1-(n-decyl)-3-carboxy-4,6-dimethylpyrid-2-one, 62.1 g. mp. 67.5°-72° C. The solid when recrystallized from methanol has a mp. of 74°-76.5° C.