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

HRID 1095784Notes

Reaction equation

HRID 1095784 reaction equation
[CH:1]1([CH2:4][O:5][C:6]2[C:7]([N+:18]([O-])=O)=[C:8]([CH:13]=[CH:14][C:15]=2[O:16][CH3:17])[C:9]([O:11][CH3:12])=[O:10])[CH2:3][CH2:2]1>[Pd].CO>[NH2:18][C:7]1[C:6]([O:5][CH2:4][CH:1]2[CH2:3][CH2:2]2)=[C:15]([O:16][CH3:17])[CH:14]=[CH:13][C:8]=1[C:9]([O:11][CH3:12])=[O:10]

Participants

4

Reactant 1

HCID 53442000Methyl 3-(cyclopropylmethoxy)-4-methoxy-2-nitrobenzoate

Product 1

HCID 53441652Methyl 2-amino-3-(cyclopropylmethoxy)-4-methoxybenzoateYield 95.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of methyl 3-(cyclopropylmethoxy)-4-methoxy-2-nitrobenzoate (128 g, 0.46 mol), 10% Pd/C (110 g, 103 mmol Pd), and methanol (1 L) was stirred overnight at room temperature under an atmosphere of H2. The resulting mixture was filtered and concentrated to give 110 g of methyl 2-amino-3-(cyclopropylmethoxy)-4-methoxybenzoate as a white solid. MS (ESI): 252.1.

Workup

  1. filtrationThe resulting mixture was filtered
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-220d446a98604ac2b7522953fb9228b4
Source dataset
uspto-grants-2012_03
Patent number
US08138205B2

Reaction notes

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