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

HRID 1195870Notes

Reaction equation

HRID 1195870 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-b448c5bef12e4fea9fae139e7d6897d8
Source dataset
uspto-grants-1992_05
Patent number
US05112846

Reaction notes

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