Hydrochloric Acid → Anthranilic acid, N-(2-methoxyphenyl)-

HRID 1980488Notes

Reaction equation

HRID 1980488 reaction equation
Cl[C:2]1[CH:10]=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].[CH3:11][O:12][C:13]1[CH:19]=[CH:18][CH:17]=[CH:16][C:14]=1[NH2:15].C(=O)([O-])[O-].[K+].[K+].Cl>CN(C)C=O>[CH3:11][O:12][C:13]1[CH:19]=[CH:18][CH:17]=[CH:16][C:14]=1[NH:15][C:2]1[CH:10]=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 70002-MethoxyanilineHCID 83742-Chlorobenzoic AcidHCID 11430Potassium Carbonate

Product 1

HCID 202774Anthranilic acid, N-(2-methoxyphenyl)-Yield 47%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of 40 g (0.25 mole) of 2-chlorobenzoic acid, 21 ml (0.26 mole) of 2-methoxyaniline, 3.84 g cupric acetate, 35.4 g of potassium carbonate and 155 ml of dimethylformamide was heated at 120° C. for 12 hours. The reaction mixture was poured into ice-water, acidified with concentrated hydrochloric acid to pH 2, and stirred for one hour. The solid product was collected by filtration, air dried and recrystallized from toluene to give 28.61 g of 2-(2-methoxyphenylamino)benzoic acid.

Workup

  1. filtrationThe solid product was collected by filtration, air
  2. customdried
  3. customrecrystallized from toluene

Sources & evidence

ORD record
ord-306546e7cdf84c17a109594c8334b072
Source dataset
uspto-grants-1985_04
Patent number
US04510139

Reaction notes

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