Sodium Hydroxide → HCID 13234020, compound

HRID 1632501Notes

Reaction equation

HRID 1632501 reaction equation
[OH-].[Na+].C([O:5][C:6]([C:8]1[C:17](=[O:18])[C:16]2[C:11](=[CH:12][C:13]([CH3:24])=[C:14]([C:19](=[O:23])[CH2:20][CH2:21][CH3:22])[CH:15]=2)[NH:10][CH:9]=1)=[O:7])C>C(O)C>[C:19]([C:14]1[CH:15]=[C:16]2[C:11](=[CH:12][C:13]=1[CH3:24])[NH:10][CH:9]=[C:8]([C:6]([OH:7])=[O:5])[C:17]2=[O:18])(=[O:23])[CH2:20][CH2:21][CH3:22]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 13234019HCID 13234019, compound

Product 1

HCID 13234020HCID 13234020, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 300 ml of ethanol and 100 ml of 2N sodium hydroxide solution is added to 50 g of 6-butyryl-7-methyl-4-oxo-1,4-dihydroquinoline-3-carboxylic acid ethyl ester and the mixture is heated to 70° and maintained at that temperature for 1 hour. The ethanol is removed, the remaining mixture is diluted with water and extracted by shaking with ether, and the aqueous phase is separated off and acidified with concentrated hydrochloric acid. The precipitated crude product is filtered off and recrystallised from ethanol. 6-Butyryl-7-methyl-4-oxo-1,4-dihydroquinoline-3-carboxylic acid having a melting point of 249°-252.5° is obtained.

Workup

  1. temperaturethe mixture is heated to 70°
  2. temperaturemaintained at that temperature for 1 hour
  3. customThe ethanol is removed
  4. additionthe remaining mixture is diluted with water
  5. extractionextracted
  6. customthe aqueous phase is separated off
  7. customThe precipitated crude product
  8. filtrationis filtered off
  9. customrecrystallised from ethanol

Sources & evidence

ORD record
ord-d6af3594d4e34a40b17c16afa126f29b
Source dataset
uspto-grants-1984_10
Patent number
US04476132

Reaction notes

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