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

HRID 14923

反応式

HRID 14923 の反応式
[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]

参加物

5

反応物 4

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

生成物 1

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

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-e0bbbaca99b84e02acf1da8cb5249a8b
出典データセット
uspto-grants-2010_06
特許番号
US07732444B2

関連ノート

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