Methanol → Benzoic acid, 2-((2,3-dimethylphenyl)amino)-, methyl ester

HRID 1461423Notes

Reaction equation

HRID 1461423 reaction equation
[CH3:1][C:2]1[C:7]([CH3:8])=[CH:6][CH:5]=[CH:4][C:3]=1[NH:9][C:10]1[CH:18]=[CH:17][CH:16]=[CH:15][C:11]=1[C:12]([OH:14])=[O:13].S(=O)(=O)(O)O.[CH3:24]O>>[CH3:1][C:2]1[C:7]([CH3:8])=[CH:6][CH:5]=[CH:4][C:3]=1[NH:9][C:10]1[CH:18]=[CH:17][CH:16]=[CH:15][C:11]=1[C:12]([O:14][CH3:24])=[O:13]

Participants

4

Reactant 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 4044Mefenamic acid

Product 1

HCID 71040Benzoic acid, 2-((2,3-dimethylphenyl)amino)-, methyl esterYield 86%

Procedure

A suspension of 2-[(2,3-dimethylphenyl) amino]benzoic acid (mefenamic acid) 35 g, 145 mmol) in methanol (600 ml) and concentrated sulfuric acid (15 ml) is heated at reflux for two days. The reaction mixture is cooled in an ice bath. The resulting solid is collected by filtration and recrystallized from methanol to give 2-[(2,3-dimethylphenyl)amino]benzoic acid, methyl ester (32.0 g, 86%); mp 98°-100° C.

Workup

  1. temperatureat reflux for two days
  2. temperatureThe reaction mixture is cooled in an ice bath
  3. filtrationThe resulting solid is collected by filtration
  4. customrecrystallized from methanol

Sources & evidence

ORD record
ord-70643c5da8e346c7ad4bb7b379d8fcfd
Source dataset
uspto-grants-1991_12
Patent number
US05075330

Reaction notes

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