Potassium tert-butoxide → Ethyl 8-chloro-1-cyclopropyl-6,7-difluoro-4-oxo-1,4-dihydroquinoline-3-carboxylate

HRID 476776

반응식

HRID 476776 반응식
[Cl:1][C:2]1[C:3](F)=[C:4]([CH:18]=[C:19]([F:22])[C:20]=1[F:21])[C:5]([C:7](=[CH:13][NH:14][CH:15]1[CH2:17][CH2:16]1)[C:8]([O:10][CH2:11][CH3:12])=[O:9])=[O:6].CC(C)([O-])C.[K+]>C(O)(C)(C)C>[Cl:1][C:2]1[C:20]([F:21])=[C:19]([F:22])[CH:18]=[C:4]2[C:3]=1[N:14]([CH:15]1[CH2:17][CH2:16]1)[CH:13]=[C:7]([C:8]([O:10][CH2:11][CH3:12])=[O:9])[C:5]2=[O:6]

참가 물질

4

반응물 2

HCID 23665647Potassium tert-butoxideHCID 178471875HCID 178471875, 화합물

생성물 1

HCID 13579166Ethyl 8-chloro-1-cyclopropyl-6,7-difluoro-4-oxo-1,4-dihydroquinoline-3-carboxylate

시약·촉매·용매 1

HCID 6386tert-Butanol용매2회

반응 조건

온도
6 °C

실험 절차

To a solution of ethyl 2-(3-chloro-2,4,5-trifluorobenzoyl)-3-cyclopropylaminoacrylate in 40 ml of dry t-butanol is added a slurry of 1.20 g (10.7 mmol) of potassium t-butoxide in 20 ml of dry t-butanol. The reaction mixture is stirred at 6° C. for eight hours, then cooled to room temperature and concentrated. The residue is dissolved in chloroform, washed with water, dried over magnesium sulfate, filtered, and concentrated to give a pale brown solid. The crude product is purified by silica gel chromatography, and eluted with 80:20 chloroform:ethyl acetate to give 1.2 g of the title compound.

후처리

  1. temperaturecooled to room temperature
  2. concentrationconcentrated
  3. dissolutionThe residue is dissolved in chloroform
  4. washwashed with water
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customto give a pale brown solid
  9. customThe crude product is purified by silica gel chromatography
  10. washeluted with 80:20 chloroform

출처 및 근거

ORD 기록
ord-9b6bc155da43466689375b0b4950888a
출처 데이터셋
uspto-grants-1989_12
특허 번호
US04885386

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