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

HRID 1964193Notes

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 mmol) in MeOH (100 mL) was added Raney Nickel (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 (petroleum ether/ethyl acetate 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, 1 H), 6.64 (d, J=2.0 Hz, 2 H), 3.64 (s, 3 H), 1.55-1.52 (m, 2 H), 1.15-1.12 (m, 2 H).

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 (petroleum ether/ethyl acetate 1:1)

Sources & evidence

ORD record: ord-d7a6385eff184d5c892cccd015591771
Source dataset: uspto-grants-2013_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08415387B2

Reaction notes

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