Hydrochloric Acid → 3-methyl-2-[(2-phenoxyacetyl)amino]benzoic Acid

HRID 1587420

Reaction equation

HRID 1587420 reaction equation
[CH3:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:4]([C:5]([OH:7])=[O:6])[C:3]=1[NH2:11].[O:12]([CH2:19][C:20](Cl)=[O:21])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.Cl>[OH-].[Na+]>[CH3:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:4]([C:5]([OH:7])=[O:6])[C:3]=1[NH:11][C:20](=[O:21])[CH2:19][O:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 69703Phenoxyacetyl chlorideHCID 781012-Amino-3-methylbenzoic acid

Product 1

HCID 35608083-methyl-2-[(2-phenoxyacetyl)amino]benzoic AcidYield 47%

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Procedure

3-Methylanthranilic acid 5 g (33 mmol) was dissolved in 10% aqueous sodium hydroxide solution 27 ml and to this solution, phenoxyacetyl chloride 6.2 g (36 mmol) was added dropwise at 0° C. The resulting solution was stirred at room temperature for 1 hour and acidified with 10% hydrochloric acid solution. Deposited crystals were collected by filtration, washed with water and recrystallized from ethanol to obtain 3-methyl-N-(phenoxyacetyl)anthranilic acid (melting point: 174° to 176° C.) 4.4 g (yield: 47%).

Workup

  1. additionwas added dropwise at 0° C
  2. filtrationDeposited crystals were collected by filtration
  3. washwashed with water
  4. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-ca19d20234ad4e699ea96efbe2252535
Source dataset
uspto-grants-1993_06
Patent number
US05217961

Linked notes

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