4-(2-Chloroethylamino)-3-nitro-benzoic Acid Methyl Ester → 3-Amino-4-(2-chloroethylamino)-benzoic acid methyl ester

HRID 555290Notes

Reaction equation

HRID 555290 reaction equation
[CH3:1][O:2][C:3](=[O:17])[C:4]1[CH:9]=[CH:8][C:7]([NH:10][CH2:11][CH2:12][Cl:13])=[C:6]([N+:14]([O-])=O)[CH:5]=1>CO.[Pd]>[CH3:1][O:2][C:3](=[O:17])[C:4]1[CH:9]=[CH:8][C:7]([NH:10][CH2:11][CH2:12][Cl:13])=[C:6]([NH2:14])[CH:5]=1

Participants

4

Reactant 1

HCID 122573344-(2-Chloroethylamino)-3-nitro-benzoic Acid Methyl Ester

Product 1

HCID 669874953-Amino-4-(2-chloroethylamino)-benzoic acid methyl esterYield 98%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of 4-(2-chloroethylamino)-3-nitro-benzoic acid methyl ester (12.7 g, 0.0492 mol) in methanol (500 mL) was added 10% Pd/C (1.3 g) under a N2 atmosphere. The reaction mixture was hydrogenated in a Parr apparatus at 3 kg pressure for 2 h. The catalyst was filtered over celite and the filtrate was concentrated affording 11.0 g (98%) of 3-amino-4-(2-chloroethylamino)-benzoic acid methyl ester as a solid.

Workup

  1. filtrationThe catalyst was filtered over celite
  2. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-85169878522e47488972aec505890d7b
Source dataset
uspto-grants-2011_11
Patent number
US08053431B2

Reaction notes

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