Methyl 1-(4-hydroxy-3-nitrophenyl)cyclopropanecarboxylate → 1-(3-Amino-4-hydroxy-phenyl)-cyclopropanecarboxylic acid methyl ester

HRID 2242680Notes

Reaction equation

[CH3:1][O:2][C:3]([C:5]1([C:8]2[CH:13]=[CH:12][C:11]([OH:14])=[C:10]([N+:15]([O-])=O)[CH:9]=2)[CH2:7][CH2:6]1)=[O:4]>CO.[Ni]>[CH3:1][O:2][C:3]([C:5]1([C:8]2[CH:13]=[CH:12][C:11]([OH:14])=[C:10]([NH2:15])[CH:9]=2)[CH2:7][CH2:6]1)=[O:4]

Participants

Conditions

Temperature: 35 °C

Procedure

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).

Workup

filtrationThe catalyst was filtered off through a Celite pad
customthe filtrate was evaporated under vacuum
customto give crude product, which
customwas purified by column chromatography on silica gel (P.E./EtOAc 1:1)

Sources & evidence

ORD record: ord-5a4d6ebfbca34f749941f156060a49eb
Source dataset: uspto-grants-2010_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07671221B2

Reaction notes

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