5-tert-butyl-6-nitro-1H-indole → HCID 57470208, 화합물

HRID 468496노트

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HRID 468496 반응식
[C:1]([C:5]1[CH:6]=[C:7]2[C:11](=[CH:12][C:13]=1[N+:14]([O-])=O)[NH:10][CH:9]=[CH:8]2)([CH3:4])([CH3:3])[CH3:2]>[Ni].CO>[C:1]([C:5]1[CH:6]=[C:7]2[C:11](=[CH:12][C:13]=1[NH2:14])[NH:10][CH:9]=[CH:8]2)([CH3:4])([CH3:2])[CH3:3]

참가 물질

4

반응물 1

HCID 574702075-tert-butyl-6-nitro-1H-indole

생성물 1

HCID 57470208HCID 57470208, 화합물수율 87.2%

시약·촉매·용매 2

HCID 935Nickel촉매HCID 887Methanol용매

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온도
30 °C

실험 절차

Raney Nickel (3 g) was added to 5-tert-butyl-6-nitro-1H-indole (15 g, 67 mmol) in methanol (100 mL). The mixture was stirred under hydrogen (1 atm) at 30° C. for 3 h. The catalyst was filtered off. The filtrate was dried over Na2SO4 and concentrated. The crude dark brown viscous oil was purified by column chromatography (10-20% ethyl acetate/petroleum ether) to give 5-tert-butyl-1H-indol-6-ylamine as a gray solid (11 g, 87%). NMR (300 MHz, DMSO-d6) δ 10.3 (br s, 1H), 7.2 (s, 1H), 6.9 (m, 1H), 6.6 (s, 1H), 6.1 (m, 1H), 4.4 (br s, 2H), 1.3 (s, 9H).

후처리

  1. filtrationThe catalyst was filtered off
  2. dry with materialThe filtrate was dried over Na2SO4
  3. concentrationconcentrated
  4. customThe crude dark brown viscous oil was purified by column chromatography (10-20% ethyl acetate/petroleum ether)

출처 및 근거

ORD 기록
ord-2836c29f3a354568b0a3f9a2a164a233
출처 데이터셋
uspto-grants-2014_01
특허 번호
US08623905B2

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