Hydrochloric Acid → 3-(benzoylamino)benzoic acid

HRID 1920505Notes

Reaction equation

HRID 1920505 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][CH:10]=1)[C:5]([OH:7])=[O:6].[OH-].[Na+].[C:13](Cl)(=[O:20])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.Cl>O>[C:13]([NH:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][CH:10]=1)[C:5]([OH:7])=[O:6])(=[O:20])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 7412Benzoyl chlorideHCID 74193-Aminobenzoic AcidHCID 14798Sodium Hydroxide2×

Product 1

HCID 2566173-(benzoylamino)benzoic acidYield 80%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

To a solution of 1.37 g of 3-aminobenzoic acid and 0.4 g of sodium hydroxide in 50 ml of water, 1.41 g of benzoyl chloride and a solution containing 0.4 g of sodium hydroxide in 5 ml of water were simultaneously added dropwise, in an ice bath, and the mixture was stirred at room temperature for 6 hours. The reaction solution was adjusted to pH 1 by addition of 1N hydrochloric acid, and thus obtained solid was collected by filtration to give 1.92 g (yield 80%) of the title compound as a white solid.

Workup

  1. additionwere simultaneously added dropwise, in an ice bath
  2. filtrationwas collected by filtration

Sources & evidence

ORD record
ord-46ac2e65fd4b453e8586f94a0cc49df5
Source dataset
uspto-grants-2012_05
Patent number
US08168825B2

Reaction notes

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