Potassium tert-butoxide → Ethyl 1-cyclopropyl-6,7-difluoro-4-oxo-1,4-dihydroquinoline-3-carboxylate

HRID 1081408Notes

Reaction equation

HRID 1081408 reaction equation
F[C:2]1[C:3](=[CH:17][C:18]([F:23])(C)[CH:19]([F:21])[CH:20]=1)[C:4]([C:6](=[CH:12][NH:13][CH:14]1[CH2:16][CH2:15]1)[C:7]([O:9][CH2:10][CH3:11])=[O:8])=[O:5].CC(C)([O-])C.[K+]>C(O)(C)(C)C>[CH:14]1([N:13]2[C:2]3[C:3](=[CH:17][C:18]([F:23])=[C:19]([F:21])[CH:20]=3)[C:4](=[O:5])[C:6]([C:7]([O:9][CH2:10][CH3:11])=[O:8])=[CH:12]2)[CH2:16][CH2:15]1

Participants

4

Reactant 2

HCID 23665647Potassium tert-butoxideHCID 178471856HCID 178471856, compound

Product 1

HCID 9817544Ethyl 1-cyclopropyl-6,7-difluoro-4-oxo-1,4-dihydroquinoline-3-carboxylateYield 65.1%

Reagents, catalysts & solvents 1

HCID 6386tert-ButanolSolvent

Conditions

Temperature
60 °C

Procedure

A solution of 7.2 g (22 mmol) of ethyl 2-(2,4,5-trifluoro-5-methylbenzoyl)-3-cyclopropylaminoacrylate in 100 mL of dry t-butanol was treated portionwise with 2.8 g (25 mmol) of potassium t-butoxide, and the reaction mixture was stirred at 60° C. for 5 hours. The suspension was cooled to room temperature and concentrated. The residue was partitioned between dichloromethane and 1N hydrochloric acid; the organic phase was washed with water, dried over magnesium sulfate, and concentrated. The crude product was slurried in boiling ethanol, filtered, and air-dried to give 4.2 g of the title compound.

Workup

  1. temperatureThe suspension was cooled to room temperature
  2. concentrationconcentrated
  3. customThe residue was partitioned between dichloromethane and 1N hydrochloric acid
  4. washthe organic phase was washed with water
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated
  7. filtrationfiltered
  8. customair-dried

Sources & evidence

ORD record
ord-0aea4dbcd937491282f71f3c781034b6
Source dataset
uspto-grants-1996_12
Patent number
US05585491

Reaction notes

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