Ethanol → 2-Methyl-6-nitro-1H-indole

HRID 2079913

반응식

HRID 2079913 반응식
[H-].[Na+].[N+:3]([C:6]1[CH:7]=[CH:8][C:9]([C:13]#[C:14][CH3:15])=[C:10]([NH2:12])[CH:11]=1)([O-:5])=[O:4].ClC(OCC)=O.[O-]CC.[Na+].C(O)C>CN(C=O)C.C(OCC)(=O)C>[CH3:15][C:14]1[NH:12][C:10]2[C:9]([CH:13]=1)=[CH:8][CH:7]=[C:6]([N+:3]([O-:5])=[O:4])[CH:11]=2

참가 물질

8

반응물 5

HCID 702EthanolHCID 10928Ethyl chloroformateHCID 24758Sodium hydrideHCID 2723922Sodium ethoxideHCID 671007405-Nitro-2-prop-1-ynyl-phenylamine

생성물 1

HCID 6005082-Methyl-6-nitro-1H-indole

시약·촉매·용매 2

HCID 6228Dimethylformamide용매2회HCID 8857Ethyl Acetate용매

실험 절차

Cool a mixture of sodium hydride (60% dispersion in oil, 0.33 g, 8.19 mmol) in anhydrous DMF to 0° C. under inert atmosphere. Add 5-nitro-2-prop-1-ynyl-phenylamine 17 (1.31 g, 7.44 mmol) in 10 mL DMF and stir 5 minutes. Add ethyl chloroformate (0.78 mL, 8.19 mmol), warm to ambient temperature, and stir 2 hours. Quench the reaction with saturated aqueous sodium bicarbonate, add ethyl acetate, and wash with saturated aqueous sodium bicarbonate followed by saturated aqueous brine. Dry the organic layer over sodium sulfate, filter, and concentrate in vacuo. Add to the residue a solution of sodium ethoxide in ethanol (0.6 M, 50 mL, 0.30 mmol) and reflux 14 hours. Cool to ambient temperature and concentrate in vacuo. Redissolve the residue in diethyl ether and wash with saturated aqueous sodium bicarbonate followed by saturated aqueous brine. Dry the organic layer over sodium sulfate, filter, concentrate in vacuo, and chromatograph the residue over silica gel, eluting with hexanes/ethyl acetate (9:1) to afford the title compound, 0.79 g (60%). LRMS (API ES−)=175.0 (M−H).

후처리

  1. temperatureCool
  2. customQuench
  3. customthe reaction with saturated aqueous sodium bicarbonate
  4. washwash with saturated aqueous sodium bicarbonate
  5. dry with materialDry the organic layer over sodium sulfate
  6. filtrationfilter
  7. concentrationconcentrate in vacuo
  8. temperaturereflux 14 hours
  9. concentrationconcentrate in vacuo
  10. dissolutionRedissolve the residue in diethyl ether
  11. washwash with saturated aqueous sodium bicarbonate
  12. dry with materialDry the organic layer over sodium sulfate
  13. filtrationfilter
  14. concentrationconcentrate in vacuo, and chromatograph the residue over silica gel
  15. washeluting with hexanes/ethyl acetate (9:1)

출처 및 근거

ORD 기록
ord-b7443fbb105549c2ac2a8095ee759b5e
출처 데이터셋
uspto-grants-2011_04
특허 번호
US07932284B2

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