Methyl 3-(4-nitrophenyl)cyclopentanecarboxylate → Methyl 3-(4-aminophenyl)cyclopentanecarboxylate

HRID 1713839Notes

Reaction equation

HRID 1713839 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([CH:10]2[CH2:14][CH2:13][CH:12]([C:15]([O:17][CH3:18])=[O:16])[CH2:11]2)=[CH:6][CH:5]=1)([O-])=O>[Pd].CCO>[NH2:1][C:4]1[CH:5]=[CH:6][C:7]([CH:10]2[CH2:14][CH2:13][CH:12]([C:15]([O:17][CH3:18])=[O:16])[CH2:11]2)=[CH:8][CH:9]=1

Participants

4

Reactant 1

HCID 59464325Methyl 3-(4-nitrophenyl)cyclopentanecarboxylate

Product 1

HCID 59464327Methyl 3-(4-aminophenyl)cyclopentanecarboxylateYield 88.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

10% palladium on carbon (78 mg) was added to a stirred solution of methyl 3-(4-nitrophenyl)cyclopentanecarboxylate (782 mg, 3.14 mmol) in EtOH (40 mL). The mixture was stirred under an atmosphere of hydrogen for 16 h then filtered through diatomaceous earth and the filter washed with EtOAc. Volatile material was removed by evaporation to give the title compound (Intermediate 84) (608 mg, 88%) as an oil; 1H NMR δ 2.24-1.45 (m, 6H), 3.03-2.83 (m, 2H), 3.62 (s, 3H), 4.80 (s, 2H), 6.53-6.46 (m, 2H), 6.92-6.86 (m, 2H); MS m/e MH+ 220.

Workup

  1. filtrationthen filtered through diatomaceous earth
  2. washthe filter washed with EtOAc
  3. customVolatile material was removed by evaporation

Sources & evidence

ORD record
ord-d6d2b3677cc046698e6be308274d84f1
Source dataset
uspto-grants-2010_09
Patent number
US07795283B2

Reaction notes

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