Quinoline → 2-Chloro-5-(trifluoromethyl)nicotinonitrile

HRID 132841

반응식

HRID 132841 반응식
P(Cl)(Cl)([Cl:3])=O.N1C2C(=CC=CC=2)C=CC=1.[C:16]([C:18]1[C:19](O)=[N:20][CH:21]=[C:22]([C:24]([F:27])([F:26])[F:25])[CH:23]=1)#[N:17].C(=O)(O)[O-].[Na+]>O>[Cl:3][C:19]1[C:18]([C:16]#[N:17])=[CH:23][C:22]([C:24]([F:27])([F:26])[F:25])=[CH:21][N:20]=1

참가 물질

6

반응물 4

HCID 7047QuinolineHCID 24813Phosphorus oxychlorideHCID 516892Sodium BicarbonateHCID 148370202-Oxo-5-(trifluoromethyl)-1,2-dihydropyridine-3-carbonitrile

생성물 1

HCID 200715992-Chloro-5-(trifluoromethyl)nicotinonitrile

시약·촉매·용매 1

HCID 962Water용매

실험 절차

To a mixture of phosphorous oxychloride (13.4 mL, 144 mmol) and quinoline (8.7 mL, 73 mmol) was added the product from Step C above (24.6 g, 131 mmol) and the resultant mixture was heated to reflux for 3 h. The reaction was cooled to 100° C. before water (70 mL) was slowly added. The mixture was further cooled to room temperature and neutralized by the cautious addition of saturated aqueous sodium bicarbonate solution. The aqueous layer was extracted with three portions of ethyl acetate and the organic layers were combined, dried over magnesium sulfate and concentrated in vacuo. The crude product was purified by flash chromatography to afford the desired compound. 1H NMR (500 MHz, CDCl3) δ 8.88 (d, J=2.0 Hz, 1H), 8.26 (d, J=2.5 Hz, 1H).

후처리

  1. temperatureto reflux for 3 h
  2. additionwas slowly added
  3. extractionThe aqueous layer was extracted with three portions of ethyl acetate
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated in vacuo
  6. customThe crude product was purified by flash chromatography

출처 및 근거

ORD 기록
ord-15754b359c6e4374b7dbfa22f34c8819
출처 데이터셋
uspto-grants-2008_06
특허 번호
US07388019B2

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