Hydrochloric Acid → 2-Chloro-4-[[(3-hydroxyphenyl)amino]carbonyl]benzoic acid

HRID 1976951Notes

Reaction equation

HRID 1976951 reaction equation
C[O:2][C:3](=[O:21])[C:4]1[CH:9]=[CH:8][C:7]([C:10]([NH:12][C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([OH:19])[CH:14]=2)=[O:11])=[CH:6][C:5]=1[Cl:20].Cl>[OH-].[Na+]>[Cl:20][C:5]1[CH:6]=[C:7]([C:10]([NH:12][C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([OH:19])[CH:14]=2)=[O:11])[CH:8]=[CH:9][C:4]=1[C:3]([OH:21])=[O:2]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 540086482-Chloro-4-[[(3-hydroxyphenyl)amino]carbonyl]benzoic acid methyl ester

Product 1

HCID 219993342-Chloro-4-[[(3-hydroxyphenyl)amino]carbonyl]benzoic acidYield 102.1%

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Procedure

A solution of 2-chloro-4-[[(3-hydroxyphenyl)amino]carbonyl]benzoic acid methyl ester (900 mg; 2.82 mmol) in an aqueous 0.5 N sodium hydroxide solution (20 mL) was stirred at room temperature under argon. After 2 hr, the solution was acidified with 1 N HCl (11 mL) and the resulting colorless solid was filtered, washed with water, and dried in vacuo to give 840 mg of 2-chloro-4-[[(3-hydroxyphenyl)amino]carbonyl]benzoic acid. FAB HRMS: (C15H12ClNO4) Obs. Mass 306.0548 Calcd. Mass 306.0533 (M+H).

Workup

  1. filtrationthe resulting colorless solid was filtered
  2. washwashed with water
  3. customdried in vacuo

Sources & evidence

ORD record
ord-c57cee9b559d4969a4a62ce8f2af95be
Source dataset
uspto-grants-2001_05
Patent number
US06229011B1

Reaction notes

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