5-Nitro-2-phenyl-1H-indole → 2-phenyl-1H-indol-5-amine

HRID 503330ノート

反応式

HRID 503330 の反応式
[N+:1]([C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[NH:9][C:8]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)=[CH:7]2)([O-])=O>CO.[Ni]>[C:13]1([C:8]2[NH:9][C:10]3[C:6]([CH:7]=2)=[CH:5][C:4]([NH2:1])=[CH:12][CH:11]=3)[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1

参加物

4

反応物 1

HCID 2803095-Nitro-2-phenyl-1H-indole

生成物 1

HCID 98371822-phenyl-1H-indol-5-amine収率 77%

試薬・触媒・溶媒 2

HCID 935Nickel触媒HCID 887Methanol溶媒

実験手順

To a solution of 5-nitro-2-phenyl-1H-indole (2.83 g, 0.01 mol) in MeOH (30 mL) was added Raney Ni (510 mg) under nitrogen atmosphere. The mixture was stirred under hydrogen atmosphere (1 atm) at room temperature overnight. The catalyst was filtered through a Celite pad and the filtrate was evaporated under vacuum to give the crude product, which was purified by column chromatography on silica gel (petroleum ether/ethyl acetate=5/1) to give 2-phenyl-1H-indol-5-amine (1.6 g, 77%). 1H NMR (400 MHz, CDCl3) δ 7.76 (d, J=7.6 Hz, 2H), 7.39 (t, J=7.6 Hz, 2H), 7.24 (t, J=7.6 Hz, 1H), 7.07 (d, J=8.4 Hz, 1H), 6.64 (d, J=1.6 Hz, 1H), 6.60 (d, J=1.2 Hz, 1H), 6.48 (dd, J=2.0, 8.4 Hz, 1H), 4.48 (brs, 2H); MS (ESI) m/e (M+H+) 209.0.

後処理

  1. filtrationThe catalyst was filtered through a Celite pad
  2. customthe filtrate was evaporated under vacuum
  3. customto give the crude product, which
  4. customwas purified by column chromatography on silica gel (petroleum ether/ethyl acetate=5/1)

出典と根拠

ORDレコード
ord-e3f80013107c4eb483682ae0f3f7fd36
出典データセット
uspto-grants-2010_08
特許番号
US07776905B2

反応ノート

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