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

HRID 1522803Notes

Reaction equation

HRID 1522803 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

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 rt 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-2f24e72be8d7419998d02b2fbfc978aa
Source dataset
uspto-grants-2015_07
Patent number
US09078887B2

Reaction notes

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