Water → 6-Ethyl-2-oxo-5-propanoyl-1,2-dihydropyridine-3-carboxylic acid

HRID 648378Notes

Reaction equation

HRID 648378 reaction equation
[CH2:1]([C:3]1[NH:4][C:5](=[O:15])[C:6](=[CH:9][C:10]=1[C:11](=[O:14])[CH2:12][CH3:13])[C:7]#N)[CH3:2].[OH2:16].S(=O)(=O)(O)[OH:18]>C(O)(=O)C>[CH2:1]([C:3]1[NH:4][C:5](=[O:15])[C:6](=[CH:9][C:10]=1[C:11](=[O:14])[CH2:12][CH3:13])[C:7]([OH:18])=[O:16])[CH3:2]

Participants

5

Reactant 3

HCID 962WaterHCID 1118Sulfuric AcidHCID 103756336-ethyl-2-oxo-5-propanoyl-1H-pyridine-3-carbonitrile

Product 1

HCID 132365116-Ethyl-2-oxo-5-propanoyl-1,2-dihydropyridine-3-carboxylic acid

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture containing 40.8 g of 6-ethyl-1,2-dihydro-2-oxo-5-(n-propanoyl)nicotinonitrile, 50 ml of water, 75 ml of concentrated sulfuric acid and 200 ml of acetic acid was heated on a steam bath for 8 hours, cooled and concentrated on a rotary evaporator to remove the acetic acid and water. The remaining mixture was diluted with 300 ml of water and chilled for 1 hour in an ice bath. The white solid that separated was collected, washed with water and dried in a vacuum over at 80° C. and recrystallized from isopropyl alcohol-ether and dried in a vacuum oven at 90° C. to yield 34.6 g of 6-ethyl-1,2-dihydro-2-oxo-5-(n-propanoyl)nicotinic acid, m.p. 180°-182° C.

Workup

  1. temperaturewas heated on a steam bath for 8 hours
  2. temperaturecooled
  3. concentrationconcentrated on a rotary evaporator
  4. customto remove the acetic acid and water
  5. additionThe remaining mixture was diluted with 300 ml of water
  6. temperaturechilled for 1 hour in an ice bath
  7. customThe white solid that separated
  8. customwas collected
  9. washwashed with water
  10. customdried in a vacuum over at 80° C.
  11. customrecrystallized from isopropyl alcohol-ether
  12. customdried in a vacuum oven at 90° C.

Sources & evidence

ORD record
ord-2ef0666e8cbf484c9e3c1d277397937e
Source dataset
uspto-grants-1983_10
Patent number
US04412077

Reaction notes

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