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

HRID 2381056Notes

Reaction equation

HRID 2381056 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-fa73410219164886a147c5099fddd8e9
Source dataset
uspto-grants-2012_09
Patent number
US08258154B2

Reaction notes

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