反応 #67412

反応方程式

1-(4-hydroxy-3-nitro-phenyl)-cyclopropanecarboxylic acid methyl ester

→

1-(3-amino-4-hydroxy-phenyl)-cyclopropanecarboxylic acid methyl ester

収率 74.0%

溶媒

MeOH

反応条件

後処理

1. 1
   ろ過The catalyst was filtered off through a Celite pad
2. 2
   その他the filtrate was evaporated under vacuum
3. 3
   その他to give crude product, which
4. 4
   その他was purified by column chromatography on silica gel (P.E./EtOAc 1:1)

実験手順

To a solution of 1-(4-hydroxy-3-nitro-phenyl)-cyclopropanecarboxylic acid methyl ester (8.3 g, 35.0 mmol) in MeOH (100 mL) was added Raney Ni (0.8 g) under nitrogen atmosphere. The mixture was stirred under hydrogen atmosphere (1 atm) at 35° C. for 8 hours. The catalyst was filtered off through a Celite pad and the filtrate was evaporated under vacuum to give crude product, which was purified by column chromatography on silica gel (P.E./EtOAc 1:1) to give 1-(3-amino-4-hydroxy-phenyl)-cyclopropanecarboxylic acid methyl ester (5.3 g, 74%). 1H NMR (CDCl3, 400 MHz) δ 6.77 (s, 1H), 6.64 (d, J=2.0 Hz, 2H), 3.64 (s, 3H), 1.55-1.52 (m, 2H), 1.15-1.12 (m, 2H).

出典