Phosphorus oxychloride → Ethyl 4-chloro-7-(trifluoromethyl)quinoline-3-carboxylate

HRID 1803769

반응식

HRID 1803769 반응식
O[C:2]1[C:11]2[C:6](=[CH:7][C:8]([C:12]([F:15])([F:14])[F:13])=[CH:9][CH:10]=2)[N:5]=[CH:4][C:3]=1[C:16]([O:18][CH2:19][CH3:20])=[O:17].P(Cl)(Cl)([Cl:23])=O>>[Cl:23][C:2]1[C:11]2[C:6](=[CH:7][C:8]([C:12]([F:15])([F:14])[F:13])=[CH:9][CH:10]=2)[N:5]=[CH:4][C:3]=1[C:16]([O:18][CH2:19][CH3:20])=[O:17]

참가 물질

3

반응물 2

HCID 24813Phosphorus oxychlorideHCID 178469560HCID 178469560, 화합물

생성물 1

HCID 14515676Ethyl 4-chloro-7-(trifluoromethyl)quinoline-3-carboxylate

실험 절차

Ethyl 4-hydroxy-7-(trifluoromethyl)quinoline-3-carboxylate (Aldrich, 10.0 g, 35.1 mmol) and phosphorus oxychloride (100 mL, 1.07 mol) were refluxed for 2 hours. After cooling the mixture was poured onto ice (1.0 L) and stirred for 1 hour. The mixture was extracted twice with dichloromethane (500 mL), dried over sodium sulfate, and concentrated under reduced pressure. The residue was chromatographed on silica gel eluting with 0-40% ethyl acetate in hexane to afford the title compound. 1H NMR (300 MHz, DMSO-d6) δ ppm 1.40 (t, J=7.12 Hz, 3H), 4.46 (q, J=7.12 Hz, 2H), 8.14 (d, J=8.82 Hz, 1H), 8.54 (s, 1H), 8.62 (d, J=8.82 Hz, 1H), 9.30 (s, 1H). MS (ESI) m/z 303.95 (M+H)+.

후처리

  1. temperatureAfter cooling the mixture
  2. additionwas poured onto ice (1.0 L)
  3. extractionThe mixture was extracted twice with dichloromethane (500 mL)
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was chromatographed on silica gel eluting with 0-40% ethyl acetate in hexane

출처 및 근거

ORD 기록
ord-ce88d842fdfe4ac7ae3b8f122aacda48
출처 데이터셋
uspto-grants-2013_01
특허 번호
US08350083B2

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