Methyl 4-((2-methoxyethyl)amino)-3-nitrobenzoate → Methyl 3-amino-4-[(2-methoxyethyl)amino]benzoate

HRID 410903Notes

Reaction equation

HRID 410903 reaction equation
[CH3:1][O:2][C:3](=[O:18])[C:4]1[CH:9]=[CH:8][C:7]([NH:10][CH2:11][CH2:12][O:13][CH3:14])=[C:6]([N+:15]([O-])=O)[CH:5]=1>CO.CCOC(C)=O.[Pd]>[CH3:1][O:2][C:3](=[O:18])[C:4]1[CH:9]=[CH:8][C:7]([NH:10][CH2:11][CH2:12][O:13][CH3:14])=[C:6]([NH2:15])[CH:5]=1

Participants

4

Reactant 1

HCID 67335214Methyl 4-((2-methoxyethyl)amino)-3-nitrobenzoate

Product 1

HCID 50742440Methyl 3-amino-4-[(2-methoxyethyl)amino]benzoateYield 94.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 21584119Ethylacetate methanolSolvent

Procedure

3-Amino-4-(2-methoxy-ethylamino)-benzoic acid methyl ester (800.0 mg) was prepared by following General Procedure B starting from 4-(2-methoxy-ethylamino)-3-nitro-benzoic acid methyl ester (960.0 mg) and Pd/C (20% by weight, 190.0 mg) in MeOH:EtOAc (1:1, 10.0 mL). The crude product was used in the next step without further purification.

Workup

  1. customThe crude product was used in the next step without further purification

Sources & evidence

ORD record
ord-9041e3f6b2594ed994089263f2040a94
Source dataset
uspto-grants-2014_06
Patent number
US08759535B2

Reaction notes

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