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

HRID 1964240Notes

Reaction equation

HRID 1964240 reaction equation
[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

Participants

4

Reactant 1

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent

Procedure

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, 2 H), 6.86 (d, J=7.8 Hz, 2 H), 4.31 (br, 2 H), 3.61 (s, 3 H), 1.55-1.50 (m, 2 H), 1.30-1.12 (m, 2 H).

Workup

  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)

Sources & evidence

ORD record
ord-43b298e9c89e4de5ab0d30935e01bd37
Source dataset
uspto-grants-2013_04
Patent number
US08415387B2

Reaction notes

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