Methyl 4-(ethylamino)-3-nitrobenzoate → Methyl 3-amino-4-(ethylamino)benzoate

HRID 410927Notes

Reaction equation

HRID 410927 reaction equation
[CH3:1][O:2][C:3](=[O:16])[C:4]1[CH:9]=[CH:8][C:7]([NH:10][CH2:11][CH3:12])=[C:6]([N+:13]([O-])=O)[CH:5]=1>CO.CCOC(C)=O.[Pd]>[CH3:1][O:2][C:3](=[O:16])[C:4]1[CH:9]=[CH:8][C:7]([NH:10][CH2:11][CH3:12])=[C:6]([NH2:13])[CH:5]=1

Participants

4

Reactant 1

HCID 20626654Methyl 4-(ethylamino)-3-nitrobenzoate

Product 1

HCID 12758354Methyl 3-amino-4-(ethylamino)benzoateYield 89%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 21584119Ethylacetate methanolSolvent

Procedure

3-Amino-4-ethylamino-benzoic acid methyl ester (6.4 g) was prepared by following General Procedure B starting from 4-ethylamino-3-nitro-benzoic acid methyl ester (8.3 g) and Pd/C (20% by weight, 170 mg) in MeOH:EtOAc (1:1, 50.0 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-c5aaf4f0ee0945bd870b00e5789052e4
Source dataset
uspto-grants-2014_06
Patent number
US08759535B2

Reaction notes

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