Sulfuric Acid → HCID 20312204, compound

HRID 2419962Notes

Reaction equation

HRID 2419962 reaction equation
[CH2:1]([N:7]1[C:12]([CH3:13])=[CH:11][C:10]([CH3:14])=[C:9]([C:15]#N)[C:8]1=[O:17])[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6].S(=O)(=O)(O)[OH:19].[OH-:23].[Na+]>O>[CH2:1]([N:7]1[C:12]([CH3:13])=[CH:11][C:10]([CH3:14])=[C:9]([C:15]([OH:19])=[O:23])[C:8]1=[O:17])[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6]

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 14798Sodium HydroxideHCID 20312193HCID 20312193, compound

Product 1

HCID 20312204HCID 20312204, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a stirred mixture of 1-(n-hexyl)-3-cyano-4,6-dimethylpyrid-2-one(222.3 g., 0.957 mole) and water (100 ml.) is added dropwise concentrated sulfuric acid (300 g.). When the addition is completed the stirred solution is heated on a steam bath for 24 hours. The solution is poured onto ice and basified with a sodium hydroxide solution and filtered. The alkaline filtrate is acidified with acetic acid and extracted with 400 ml. of toluene. The toluene layer is then extracted with 2 × 350 ml. of 5% NaOH. The aqueous layer is acidified with hydrochloric acid and cooled in an ice bath. The semi-solid precipitate is recrystallized from methanol/water to give 1-(n-hexyl)-3-carboxy-4,6-dimethylpyrid-2-one, 24 g. (100% yield), mp. 79°-82.5°.

Workup

  1. additionWhen the addition
  2. temperatureis heated on a steam bath for 24 hours
  3. additionThe solution is poured onto ice
  4. filtrationfiltered
  5. extractionextracted with 400 ml
  6. extractionThe toluene layer is then extracted with 2 × 350 ml
  7. temperaturecooled in an ice bath
  8. customThe semi-solid precipitate is recrystallized from methanol/water

Sources & evidence

ORD record
ord-489f283b7e7d436fba772dd3d5c3f90b
Source dataset
uspto-grants-1978_08
Patent number
US04108630

Reaction notes

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