Nitromethane → 5-(2-nitro-vinyl)-1H-indole

HRID 14923

반응식

HRID 14923 반응식
[CH:1]([C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[NH:8][CH:7]=[CH:6]2)=O.CCOC(C)=O.CCCCCC.[N+:24]([CH3:27])([O-:26])=[O:25]>>[N+:24]([CH:27]=[CH:1][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[NH:8][CH:7]=[CH:6]2)([O-:26])=[O:25]

참가 물질

5

반응물 4

HCID 6375NitromethaneHCID 8058HexaneHCID 8857Ethyl AcetateHCID 589040Indole-5-carboxaldehyde

생성물 1

HCID 544650165-(2-nitro-vinyl)-1H-indole수율 11%

실험 절차

5-Formyl indole (14.5 g) was refluxed with NH4OAc (10.0 g) in nitromethane ((100 mL) for 3 hours. The mixture was cooled and evaporated under reduced pressure. The residue was recrystallized from isopropanol to give the first portion of intermediate and the mother liquid was purified by chromatograph (EtOAc:hexane=1:4 to 2:3) to the second portion intermediate of 5-(2-nitro-vinyl)-1H-indole (2.09 g combined, in 11% yield), which was treated with NaBH4 (1.85 g) in methanol (150 mL) at room temperature for 35 min then quenched with acetic acid (4 mL), concentrated and followed by chromatography purification (EtOAc:hexane=1:9) to afford 5-(2-nitro-ethyl)-1H-indole (1.37 g) in 65% yield. This nitro compound was hydrogenated with Pd—C (10%) under atmosphere hydrogen in methanol overnight to afford 2-(1H-indol-5-yl)-ethylamine in 99% yield. LC-MS showed the product had the expected M+H+ of 161.

후처리

  1. temperatureThe mixture was cooled
  2. customevaporated under reduced pressure
  3. customThe residue was recrystallized from isopropanol
  4. customto give the first portion of intermediate

출처 및 근거

ORD 기록
ord-e0bbbaca99b84e02acf1da8cb5249a8b
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07732444B2

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