Ethanol → 2-(4-cyclohexylphenyl)-6-fluoro-3-methylquinoline-4-carboxylic acid

HRID 2118651Notes

Reaction equation

HRID 2118651 reaction equation
[F:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6](=[O:11])[C:5]2=O.[CH2:13]1[CH2:18][CH2:17][CH:16]([CH:19]([CH3:28])[C:20]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24]C=2)=O)[CH2:15][CH2:14]1.[OH-:29].[K+].[CH2:31](O)C>O>[CH:16]1([C:19]2[CH:20]=[CH:22][C:27]([C:26]3[C:25]([CH3:24])=[C:5]([C:6]([OH:11])=[O:29])[C:4]4[C:8](=[CH:9][CH:10]=[C:2]([F:1])[CH:3]=4)[N:7]=3)=[CH:31][CH:28]=2)[CH2:15][CH2:14][CH2:13][CH2:18][CH2:17]1

Participants

6

Reactant 4

HCID 702EthanolHCID 14797Potassium HydroxideHCID 2365665-FluoroisatinHCID 67928556HCID 67928556, compound

Product 1

HCID 51671812-(4-cyclohexylphenyl)-6-fluoro-3-methylquinoline-4-carboxylic acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

5-Fluoroisatin (100 g, 0.61 mole) and 4-cyclohexylpropiophenone (131 g, 0.61 mole) were suspended in 1100 ml of ethanol and stirred mechanically as a solution of 219 g (5.5 mole) of KOH in 550 ml of water was added dropwise. After the addition was complete, the mixture was heated at reflux for 12 hours, cooled, and the ethanol evaporated under reduced pressure. The resulting solid was dissolved in water and washed with ethyl ether. The aqueous layer was acidified with HCl. The resulting precipitate was filtered and dried. Recrystallization from dimethylformamide and water gave 117 g of 2-(4-cyclohexylphenyl)-6-fluoro-3-methylquinoline-4-carboxylic acid, m.p. 316°-323°.

Workup

  1. additionwas added dropwise
  2. additionAfter the addition
  3. temperaturethe mixture was heated
  4. temperatureat reflux for 12 hours
  5. temperaturecooled
  6. customthe ethanol evaporated under reduced pressure
  7. dissolutionThe resulting solid was dissolved in water
  8. washwashed with ethyl ether
  9. filtrationThe resulting precipitate was filtered
  10. customdried
  11. customRecrystallization from dimethylformamide and water

Sources & evidence

ORD record
ord-499d771823494a9fa1ecacf0fdcc3ffd
Source dataset
uspto-grants-1987_07
Patent number
US04680299

Reaction notes

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