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

HRID 1081408
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인쇄 미리보기

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HRID 1081408 반응식
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
참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트

참가 물질

4

반응물 2

HCID 23665647Potassium tert-butoxideHCID 178471856HCID 178471856, 화합물

생성물 1

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

시약·촉매·용매 1

HCID 6386tert-Butanol용매

반응 조건

온도
60 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-0aea4dbcd937491282f71f3c781034b6
출처 데이터셋
uspto-grants-1996_12
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US05585491

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