Hydrochloric Acid → 2-Methyl-4-((2-methylbenzoyl)amino)benzoic acid

HRID 2389243Notes

Reaction equation

HRID 2389243 reaction equation
ClC[C:3]([C:5]1[CH:10]=[CH:9][C:8]([NH:11][C:12](=[O:20])[C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[CH3:19])=[CH:7][C:6]=1[CH3:21])=[O:4].ClCC(C1C=CC(C)=CC=1NC(=O)C1C=CC=CC=1C)=[O:25].Cl>C1(C)C=CC=CC=1>[CH3:21][C:6]1[CH:7]=[C:8]([NH:11][C:12](=[O:20])[C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[CH3:19])[CH:9]=[CH:10][C:5]=1[C:3]([OH:4])=[O:25]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 45117936N-[2-(Chloroacetyl)-5-methylphenyl]-2-methylbenzamideHCID 860993932-Chloro-2'-methyl-4'-(2-methylbenzoylamino)acetophenone

Product 1

HCID 251921172-Methyl-4-((2-methylbenzoyl)amino)benzoic acidYield 86%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A toluene solution of a mixture of 2-chloro-2′-methyl-4′-(2-methylbenzoylamino)acetophenone and 2-chloro-4′-methyl-2′-(2-methylbenzoylamino)acetophenone obtained in the above Reference Example 5 is concentrated and to the residue is added isopropyl alcohol (twice volume). To the mixture is added dropwise an aqueous sodium hypochlorite solution (twice molar amount) at 10-20° C. After completion of the reaction (30 minutes to one hour), the reaction mixture is acidified with hydrochloric acid, and the precipitated crystals are separated by filtration to give a crude product of 2-methyl-4-(2-methylbenzoylamino)benzoic acid in a yield of 86-100%. This crude product is recrystallized from methanol to give the desired product (yield 57%, purity by HPLC 99.3%).

Workup

  1. customobtained in the above Reference Example 5
  2. concentrationis concentrated and to the residue
  3. additionis added isopropyl alcohol (twice volume)
  4. additionTo the mixture is added dropwise an aqueous sodium hypochlorite solution (twice molar amount) at 10-20° C
  5. customAfter completion of the reaction (30 minutes to one hour)
  6. customthe precipitated crystals are separated by filtration

Sources & evidence

ORD record
ord-1b8f3350887e4e1fbf1f0471e4b1dffe
Source dataset
uspto-grants-2012_09
Patent number
US08273735B2

Reaction notes

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