Potassium tert-butoxide → Ethyl 1-cyclopropyl-6,7,8-trifluoro-5-methyl-1,4-dihydro-4-oxoquinoline-3-carboxylate

HRID 1081395Notes

Reaction equation

HRID 1081395 reaction equation
F[C:2]1[C:3](=[CH:17][C:18]([F:24])(C)[CH:19]([F:22])[C:20]=1[F:21])[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].[CH3:25]C(C)([O-])C.[K+]>C(O)(C)(C)C>[CH:14]1([N:13]2[C:2]3[C:3](=[C:17]([CH3:25])[C:18]([F:24])=[C:19]([F:22])[C:20]=3[F:21])[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 178471858HCID 178471858, compound

Product 1

HCID 14651259Ethyl 1-cyclopropyl-6,7,8-trifluoro-5-methyl-1,4-dihydro-4-oxoquinoline-3-carboxylateYield 54.9%

Reagents, catalysts & solvents 1

HCID 6386tert-ButanolSolvent2×

Conditions

Temperature
60 °C

Procedure

To a mixture of 9.05 g (26.3 mmol) of ethyl 2-(2,3,4,5-tetrafluoro-5-methylbenzoyl)-3-cyclopropylaminoacrylate in 100 mL of dry t-butanol was added a slurry of 3.25 g (29.0 mmol) of potassium t-butoxide in 20 mL of dry t-butanol, and the mixture was stirred at 60° C. for 4 hours. The suspension was cooled to room temperature and concentrated to a paste which was partitioned between dichloromethane and 1N hydrochloric acid. The organic layer was separated, dried over magnesium sulfate, and concentrated. Recrystallization from ethyl acetate:hexane gave 4.70 g of the title compound, mp 176°-177° C.

Workup

  1. temperatureThe suspension was cooled to room temperature
  2. concentrationconcentrated to a paste which
  3. customwas partitioned between dichloromethane and 1N hydrochloric acid
  4. customThe organic layer was separated
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated
  7. customRecrystallization from ethyl acetate

Sources & evidence

ORD record
ord-cc77184763c0441dba298e0de8b2514c
Source dataset
uspto-grants-1996_12
Patent number
US05585491

Reaction notes

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