Methyl 3-(cyclopentyloxy)-4-methoxy-2-nitrobenzoate → Methyl 2-amino-3-(cyclopentyloxy)-4-methoxybenzoate

HRID 1095763Notes

Reaction equation

HRID 1095763 reaction equation
[CH:1]1([O:6][C:7]2[C:8]([N+:19]([O-])=O)=[C:9]([CH:14]=[CH:15][C:16]=2[O:17][CH3:18])[C:10]([O:12][CH3:13])=[O:11])[CH2:5][CH2:4][CH2:3][CH2:2]1>[Pd].CO>[NH2:19][C:8]1[C:7]([O:6][CH:1]2[CH2:2][CH2:3][CH2:4][CH2:5]2)=[C:16]([O:17][CH3:18])[CH:15]=[CH:14][C:9]=1[C:10]([O:12][CH3:13])=[O:11]

Participants

4

Reactant 1

HCID 66781723Methyl 3-(cyclopentyloxy)-4-methoxy-2-nitrobenzoate

Product 1

HCID 66781747Methyl 2-amino-3-(cyclopentyloxy)-4-methoxybenzoate

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Conditions

Temperature
23 °C

Procedure

A mixture of methyl 3-(cyclopentyloxy)-4-methoxy-2-nitrobenzoate (750 mg, 2.54 mmol), 10% Pd/C (50% H2O, 500 mg, 0.23 mmol Pd), and methanol (10 mL) was stirred vigorously at 23° C. under an atmosphere of H2. After 21 h, the mixture was filtered through Celite and concentrated to give methyl 2-amino-3-(cyclopentyloxy)-4-methoxybenzoate: MS (ESI): 266.5.

Workup

  1. filtrationthe mixture was filtered through Celite
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-20d385e861a541a3b3b383c84a0a6184
Source dataset
uspto-grants-2012_03
Patent number
US08138205B2

Reaction notes

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