1-(4-Nitro-phenyl)-cyclopropanecarboxylic acid methyl ester → Methyl 1-(4-aminophenyl)cyclopropane-1-carboxylate

HRID 1847354ノート

反応式

HRID 1847354 の反応式
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10]2([C:13]([O:15][CH3:16])=[O:14])[CH2:12][CH2:11]2)=[CH:6][CH:5]=1)([O-])=O>CO.[Ni]>[NH2:1][C:4]1[CH:5]=[CH:6][C:7]([C:10]2([C:13]([O:15][CH3:16])=[O:14])[CH2:12][CH2:11]2)=[CH:8][CH:9]=1

参加物

4

反応物 1

HCID 591294291-(4-Nitro-phenyl)-cyclopropanecarboxylic acid methyl ester

生成物 1

HCID 58841079Methyl 1-(4-aminophenyl)cyclopropane-1-carboxylate収率 66.1%

試薬・触媒・溶媒 2

HCID 935Nickel触媒HCID 887Methanol溶媒

実験手順

To a solution of methyl 1-(4-nitrophenyl)cyclopropanecarboxylate (20 g, 0.09 mol) in MeOH (400 mL) was added Ni (2 g) under nitrogen atmosphere. The mixture was stirred under hydrogen atmosphere (1 atm) at room temperature overnight. The catalyst was filtered off through a pad of Celite and the filtrate was evaporated under vacuum to give crude product, which was purified by chromatography column on silica gel (petroleum ether/ethyl acetate=10:1) to give methyl 1-(4-aminophenyl)cyclopropanecarboxylate (11.38 g, 66%). 1H NMR (300 MHz, CDCl3) δ 7.16 (d, J=8.1 Hz, 2H), 6.86 (d, J=7.8 Hz, 2H), 4.31 (br, 2H), 3.61 (s, 3H), 1.55-1.50 (m, 2H), 1.30-1.12 (m, 2H).

後処理

  1. filtrationThe catalyst was filtered off through a pad of Celite
  2. customthe filtrate was evaporated under vacuum
  3. customto give crude product, which
  4. customwas purified by chromatography column on silica gel (petroleum ether/ethyl acetate=10:1)

出典と根拠

ORDレコード
ord-d5f53d2b9e264b08877a22e86d9ece0b
出典データセット
uspto-grants-2015_02
特許番号
US08952050B2

反応ノート

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