Water → 6-Butyryl-7,8-dimethyl-4-oxo-1,4-dihydroquinoline-2-carboxylic acid

HRID 1632507Notes

Reaction equation

HRID 1632507 reaction equation
C[O:2][C:3]([C:5]1[NH:6][C:7]2[C:12]([C:13](=[O:15])[CH:14]=1)=[CH:11][C:10]([C:16](=[O:20])[CH2:17][CH2:18][CH3:19])=[C:9]([CH3:21])[C:8]=2[CH3:22])=[O:4].[OH-].[K+].O>CO>[C:16]([C:10]1[CH:11]=[C:12]2[C:7](=[C:8]([CH3:22])[C:9]=1[CH3:21])[NH:6][C:5]([C:3]([OH:4])=[O:2])=[CH:14][C:13]2=[O:15])(=[O:20])[CH2:17][CH2:18][CH3:19]

Participants

5

Reactant 3

HCID 962WaterHCID 14797Potassium HydroxideHCID 13234025HCID 13234025, compound

Product 1

HCID 132340266-Butyryl-7,8-dimethyl-4-oxo-1,4-dihydroquinoline-2-carboxylic acid

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

6.1 g of 6-butyryl-7,8-dimethyl-4-oxo-1,4-dihydroquinoline-2-carboxylic acid methyl ester are heated under reflux for 4 hours together with 3.66 g of potassium hydroxide, 1.46 ml of water and 64.4 ml of methanol. The reaction mixture is concentrated to dryness by evaporation, partitioned between ethyl acetate and water, the aqueous phases are acidified and the precipitated crystals are filtered with suction and washed with water. The 6-butyryl-7,8-dimethyl-4-oxo-1,4-dihydroquinoline-2-carboxylic acid obtained in this manner melts at 267°-269° after recrystallisation from methanol/ethanol.

Workup

  1. concentrationThe reaction mixture is concentrated to dryness by evaporation
  2. custompartitioned between ethyl acetate and water
  3. filtrationthe precipitated crystals are filtered with suction
  4. washwashed with water

Sources & evidence

ORD record
ord-a6098c2fe75e4ae98a95a0db71df69cd
Source dataset
uspto-grants-1984_10
Patent number
US04476132

Reaction notes

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