(E)-2-(5-fluoro-2,4-dinitrophenyl)-N,N-dimethylethenamine → 5-Fluoro-1H-indol-6-amine

HRID 1403982

반응식

HRID 1403982 반응식
[F:1][C:2]1[C:3]([N+:16]([O-])=O)=[CH:4][C:5]([N+:13]([O-])=O)=[C:6](/[CH:8]=[CH:9]/N(C)C)[CH:7]=1>[Ni].CCO>[F:1][C:2]1[CH:7]=[C:6]2[C:5](=[CH:4][C:3]=1[NH2:16])[NH:13][CH:9]=[CH:8]2

참가 물질

4

반응물 1

HCID 15022335(E)-2-(5-fluoro-2,4-dinitrophenyl)-N,N-dimethylethenamine

생성물 1

HCID 150223365-Fluoro-1H-indol-6-amine수율 21.5%

시약·촉매·용매 2

HCID 935Nickel촉매HCID 702Ethanol용매

실험 절차

A suspension of (E)-2-(5-fluoro-2,4-dinitrophenyl)-N,N-dimethylethenamine (8.0 g, 31 mmol) and Raney Nickel (8 g) in EtOH (80 mL) was stirred under H2 (40 psi) at room temperature for 1 h. After filtration, the filtrate was concentrated and the residue was purified by column chromatography (petroleum ether/ethyl acetate=5/1) to give 5-fluoro-1H-indol-6-amine (1.0 g, 16%) as a brown solid. 1HNMR (DMSO-d6) δ 10.56 (br s, 1H), 7.07 (d, J=12 Hz, 1H), 7.02 (m, 1H), 6.71 (d, J=8 Hz, 1H), 6.17 (s, 1H), 3.91 (br s, 2H); MS (ESI) m/e (M+H+) 150.1.

후처리

  1. filtrationAfter filtration
  2. concentrationthe filtrate was concentrated
  3. customthe residue was purified by column chromatography (petroleum ether/ethyl acetate=5/1)

출처 및 근거

ORD 기록
ord-60591861010e4e77b9d68b5c746e7ca8
출처 데이터셋
uspto-grants-2014_12
특허 번호
US08912199B2

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