4-nitro-1H-indole-2-carbonitrile → 6-Amino-1H-indole-2-carbonitrile

HRID 469956ノート

反応式

HRID 469956 の反応式
[N+:1]([C:4]1[CH:12]=[C:11]2[C:7]([CH:8]=[C:9]([C:13]#[N:14])[NH:10]2)=[CH:6][CH:5]=1)([O-])=O.[N+](C1C=CC=C2C=1C=C(C#N)N2)([O-])=O>CCO.[Ni]>[NH2:1][C:4]1[CH:12]=[C:11]2[C:7]([CH:8]=[C:9]([C:13]#[N:14])[NH:10]2)=[CH:6][CH:5]=1

参加物

5

反応物 2

HCID 143689034-nitro-1H-indole-2-carbonitrileHCID 574701946-nitro-1H-indole-2-carbonitrile

生成物 1

HCID 451170156-Amino-1H-indole-2-carbonitrile

試薬・触媒・溶媒 2

HCID 935Nickel触媒HCID 702Ethanol溶媒

実験手順

A mixture of 6-nitro-1H-indole-2-carbonitrile and 4-nitro-1H-indole-2-carbonitrile (2.5 g, 13.4 mmol) and Raney Ni (500 mg) in EtOH (50 mL) was stirred at room temperature under H2 (1 atm) for 1 h. Raney Ni was filtered off. The filtrate was evaporated under reduced pressure and purified by column chromatography to give 6-amino-1H-indole-2-carbonitrile (B-5) (1 g, 49%). 1H NMR (DMSO-d6) δ 12.75 (br s, 1 H), 7.82 (d, J=8 Hz, 1 H), 7.57 (s, 1 H), 7.42 (s, 1 H), 7.15 (d, J=8 Hz, 1 H); ESI-MS 158.2 m/z (MH+).

後処理

  1. filtrationRaney Ni was filtered off
  2. customThe filtrate was evaporated under reduced pressure
  3. custompurified by column chromatography

出典と根拠

ORDレコード
ord-4385d5518ed440fdbb31389e8f710de3
出典データセット
uspto-grants-2014_01
特許番号
US08629162B2

反応ノート

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