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

HRID 1662155ノート

反応式

HRID 1662155 の反応式
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]

参加物

3

反応物 2

HCID 24813Phosphorus oxychlorideHCID 178469560HCID 178469560、化合物

生成物 1

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

実験手順

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)+.

後処理

  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

出典と根拠

ORDレコード
ord-aeebefbea69d4f3ea9a7665a89bdcfda
出典データセット
uspto-grants-2011_10
特許番号
US08030504B2

反応ノート

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