6-Nitro-1H-indole-3-carbonitrile → 6-amino-1H-indole-3-carbonitrile

HRID 468389

反応式

HRID 468389 の反応式
[N+:1]([C:4]1[CH:12]=[C:11]2[C:7]([C:8]([C:13]#[N:14])=[CH:9][NH:10]2)=[CH:6][CH:5]=1)([O-])=O>CCO.[Pd]>[NH2:1][C:4]1[CH:12]=[C:11]2[C:7]([C:8]([C:13]#[N:14])=[CH:9][NH:10]2)=[CH:6][CH:5]=1

参加物

4

反応物 1

HCID 2831796-Nitro-1H-indole-3-carbonitrile

生成物 1

HCID 444104646-amino-1H-indole-3-carbonitrile収率 98%

試薬・触媒・溶媒 2

HCID 23938Palladium触媒HCID 702Ethanol溶媒

実験手順

A suspension of 6-nitro-1H-indole-3-carbonitrile (4.6 g, 25 mmol) and 10% Pd—C (0.46 g) in EtOH (50 mL) was stirred under H2 (1 atm) at room temperature overnight. After filtration, the filtrate was concentrated and the residue was purified by column chromatography on silica gel (petroleum ether/ethyl acetate=3/1) to give 6-amino-1H-indole-3-carbonitrile (1.0 g, 98%) as a pink solid, 1H NMR (DMSO-d6) δ 11.51 (s, 1H), 7.84 (d, J=2.4 Hz, 1H), 7.22 (d, J=8.4 Hz, 1H), 6.62 (s, 1H), 6.56 (d, J=8.4 Hz, 1H), 5.0 (s, 2H); MS (ESI) m/e (M+H+) 157.1.

後処理

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

出典と根拠

ORDレコード
ord-548bf1649087497b9b978a55ae47a6df
出典データセット
uspto-grants-2014_01
特許番号
US08623905B2

関連ノート

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