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

HRID 1081395
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HRID 1081395 반응식
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
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참가 물질

4

반응물 2

HCID 23665647Potassium tert-butoxideHCID 178471858HCID 178471858, 화합물

생성물 1

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

시약·촉매·용매 1

HCID 6386tert-Butanol용매2회

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온도
60 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-cc77184763c0441dba298e0de8b2514c
출처 데이터셋
uspto-grants-1996_12
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US05585491

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