Réaction #67412

Équation de réaction

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

→

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

Rendement 74.0%

Solvants

MeOH

Conditions de réaction

Traitement

1. 1
   FiltrationThe catalyst was filtered off through a Celite pad
2. 2
   Autrethe filtrate was evaporated under vacuum
3. 3
   Autreto give crude product, which
4. 4
   Autrewas purified by column chromatography on silica gel (P.E./EtOAc 1:1)

Mode opératoire

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).

Source