Ammonia → 4-(2-Amino-4-nitrophenylamino)benzoic acid ethyl ester

HRID 1595178Notes

Reaction equation

HRID 1595178 reaction equation
[CH2:1]([O:3][C:4](=[O:24])[C:5]1[CH:10]=[CH:9][C:8]([NH:11][C:12]2[CH:17]=[CH:16][C:15]([N+:18]([O-:20])=[O:19])=[CH:14][C:13]=2[N+:21]([O-])=O)=[CH:7][CH:6]=1)[CH3:2].[Cl-].[NH4+].N.[S-2].[Na+].[Na+]>O.C(O)C>[CH2:1]([O:3][C:4](=[O:24])[C:5]1[CH:6]=[CH:7][C:8]([NH:11][C:12]2[CH:17]=[CH:16][C:15]([N+:18]([O-:20])=[O:19])=[CH:14][C:13]=2[NH2:21])=[CH:9][CH:10]=1)[CH3:2]

Participants

7

Reactant 4

HCID 222AmmoniaHCID 14804Sodium SulfideHCID 25517Ammonium ChlorideHCID 4763896Ethyl 4-[(2,4-dinitrophenyl)amino]benzoate

Product 1

HCID 544420634-(2-Amino-4-nitrophenylamino)benzoic acid ethyl esterYield 104.5%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

At an internal temperature of 78° C. (90° C. bath temperature), 566 mg (1.7 mmol) of 4-(2,4-dinitrophenylamino)benzoic acid ethyl ester, 761 mg (12.2 mmol) of ammonium chloride, 0.68 ml of concentrated ammonia, 15 ml of ethanol and 6 ml of distilled water are combined. To this mixture is added 1.27 g (5.68 mmol) of sodium sulfide (35% strength) in 3 portions, and the mixture is stirred for one hour. The batch is vacuum-filtered at room temperature and first washed with water and then under ether, thus obtaining 535 mg of 4-(2-amino-4-nitrophenylamino)benzoic acid ethyl ester as the crude product (processed without further purification).

Workup

  1. filtrationThe batch is vacuum-filtered at room temperature
  2. washfirst washed with water

Sources & evidence

ORD record
ord-6bc4b60acd3f48858177b1f825784183
Source dataset
uspto-grants-2001_09
Patent number
US06288065B1

Reaction notes

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