Dimethylformamide → 5-Chloro-3-formyl-7-nitro-2-phenyl-1H-indole

HRID 1466478노트

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HRID 1466478 반응식
[N+:1]([C:4]1[CH:5]=[C:6]([Cl:19])[CH:7]=[C:8]2[C:12]=1[NH:11][C:10]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)=[CH:9]2)([O-:3])=[O:2].P(Cl)(Cl)(OCl)=O.CN([CH:29]=[O:30])C>ClCCl>[Cl:19][C:6]1[CH:7]=[C:8]2[C:12](=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=1)[NH:11][C:10]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)=[C:9]2[CH:29]=[O:30]

참가 물질

5

반응물 3

HCID 6228DimethylformamideHCID 684721085-chloro-7-nitro-2-phenyl-1H-indoleHCID 86587839Phosphoryloxychloride

생성물 1

HCID 866438345-Chloro-3-formyl-7-nitro-2-phenyl-1H-indole수율 45.3%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

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온도
0 °C

실험 절차

7-Nitro-5-chloro-2-phenyl-1H-indole (1.0 g, 3.67 mmol) prepared in Preparation 26 was dissolved in dichloromethane (20 mL). Phosphoryloxychloride (0.84 g, 5.50 mmol) and DMF (0.80 g, 11.01 mmol) were added in drops thereto at 0° C., and the mixture was stirred for 6 h at room temperature. After completion of the reaction, the reaction was quenched by saturated aqueous sodium hydrogen carbonate solution. The reaction mixture was extracted with ethyl acetate, washed with saturated aqueous sodium chloride solution, dried over anhydrous magnesium sulfate, and filtered. The solvent was removed under reduced pressure, and the residue was purified by column chromatography to give the title compound (0.5 g, Yield 45%).

후처리

  1. customAfter completion of the reaction
  2. customthe reaction was quenched by saturated aqueous sodium hydrogen carbonate solution
  3. extractionThe reaction mixture was extracted with ethyl acetate
  4. washwashed with saturated aqueous sodium chloride solution
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. customThe solvent was removed under reduced pressure
  8. customthe residue was purified by column chromatography

출처 및 근거

ORD 기록
ord-d21f37f80e3044ca96c055590a9f99ab
출처 데이터셋
uspto-grants-2015_04
특허 번호
US09000028B2

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