Water → HCID 20312182, compound

HRID 259379Notes

Reaction equation

HRID 259379 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

4

Reactant 3

HCID 962WaterHCID 1118Sulfuric AcidHCID 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.

Workup

  1. additionis slowly added
  2. temperaturewhile maintaining the reaction temperature below 75° C
  3. temperatureThe reaction mixture is then heated on a steam bath for 23 hours
  4. customThe cooled reaction mixture
  5. additionis poured onto ice (700 g.)
  6. additionthe reaction mixture is diluted to 2300 ml
  7. filtrationThe solid is collected by filtration
  8. customtriturated with dilute sodium hydroxide
  9. filtrationfiltered
  10. filtrationThe resulting solid is collected by filtration and vacuum
  11. customdried

Sources & evidence

ORD record
ord-9380a77cbfaf46fea14c785989be7297
Source dataset
uspto-grants-1977_07
Patent number
US04038065

Reaction notes

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