Ammonia → (1-Tosyl-1H-indol-4-YL)methanamine

HRID 41547

反応式

HRID 41547 の反応式
[S:1]([N:11]1[C:19]2[CH:18]=[CH:17][CH:16]=[C:15]([C:20]#[N:21])[C:14]=2[CH:13]=[CH:12]1)([C:4]1[CH:10]=[CH:9][C:7]([CH3:8])=[CH:6][CH:5]=1)(=[O:3])=[O:2].N>CO.[Ni]>[S:1]([N:11]1[C:19]2[C:14](=[C:15]([CH2:20][NH2:21])[CH:16]=[CH:17][CH:18]=2)[CH:13]=[CH:12]1)([C:4]1[CH:5]=[CH:6][C:7]([CH3:8])=[CH:9][CH:10]=1)(=[O:2])=[O:3]

参加物

5

反応物 2

HCID 222AmmoniaHCID 137163751-Tosyl-1H-indole-4-carbonitrile

生成物 1

HCID 67262154(1-Tosyl-1H-indol-4-YL)methanamine収率 88.6%

試薬・触媒・溶媒 2

HCID 935Nickel触媒HCID 887Methanol溶媒2 回

実験手順

A mixture of 1-tosyl-1H-indole-4-carbonitrile (0.5 g, 1.69 mmol), 5% NH3 in methanol (5.0 mL) and Raney Nickel (0.2 g) in methanol (15.0 ml) was hydrogenated at 5 Torr for 6 h at rt. After completion of the reaction, the Raney Nickel was filtered off through a pad of celite under vacuum and washed with methanol (5×2 mL). The combined filtrates were evaporated to dryness under reduced pressure. The residue was washed with 10% diethyl ether in pentane to yield the title compound as a white solid (0.45 g, 78%). [1H-NMR (CDCl3, 300 MHz): δ 7.72-7.59 (m, 3H), 7.44-7.52 (m, 1H), 7.33-6.72 (m, 5H), 4.12-4.01 (m, 2H), 2.27 (s, 3H)].

後処理

  1. customAfter completion of the reaction
  2. filtrationthe Raney Nickel was filtered off through a pad of celite under vacuum
  3. washwashed with methanol (5×2 mL)
  4. customThe combined filtrates were evaporated to dryness under reduced pressure
  5. washThe residue was washed with 10% diethyl ether in pentane

出典と根拠

ORDレコード
ord-699084edd45e4d50b35f9649ae0d7ad8
出典データセット
uspto-grants-2013_09
特許番号
US08530648B2

関連ノート

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