4-Aminobenzoic Acid → 4-[(4-Nitrobenzoyl)amino]benzoic acid

HRID 2305327Notes

Reaction equation

HRID 2305327 reaction equation
[N+:1]([C:4]1[CH:12]=[CH:11][C:7]([C:8](Cl)=[O:9])=[CH:6][CH:5]=1)([O-:3])=[O:2].[NH2:13][C:14]1[CH:22]=[CH:21][C:17]([C:18]([OH:20])=[O:19])=[CH:16][CH:15]=1.CC(N(C)C)=O>C(Cl)Cl>[N+:1]([C:4]1[CH:12]=[CH:11][C:7]([C:8]([NH:13][C:14]2[CH:22]=[CH:21][C:17]([C:18]([OH:20])=[O:19])=[CH:16][CH:15]=2)=[O:9])=[CH:6][CH:5]=1)([O-:3])=[O:2]

Participants

5

Reactant 3

HCID 9784-Aminobenzoic AcidHCID 85024-Nitrobenzoyl chlorideHCID 31374Dimethylacetamide

Product 1

HCID 4590084-[(4-Nitrobenzoyl)amino]benzoic acidYield 94%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

10 g of 4-nitrobenzoic acid chloride are slowly introduced into 7.4 g of 4-aminobenzoic acid and 36 ml of dimethylacetamide while maintaining the temperature at less than 25° C. After stirring for 24 hours, 50 ml of methylene chloride are added at 10° C. in order to precipitate the desired product. After washing with water and drying, 14.5 g of product are isolated.

Workup

  1. temperaturewhile maintaining the temperature at less than 25° C
  2. customto precipitate the desired product
  3. washAfter washing with water
  4. customdrying

Sources & evidence

ORD record
ord-593aac21eaea4ef68a1f68549fbcabaa
Source dataset
uspto-grants-2002_08
Patent number
US06440956B1

Reaction notes

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