Dimethylformamide → 2-[(4-Methoxyphenyl)amino]benzoic acid

HRID 464786

Reaction equation

HRID 464786 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][C:16]([NH2:17])=[CH:15][CH:14]=1.C(=O)([O-])[O-].[K+].[K+].CN(C)C=O>O>[CH3:11][O:12][C:13]1[CH:19]=[CH:18][C:16]([NH:17][C:2]2[CH:10]=[CH:9][CH:8]=[CH:7][C:3]=2[C:4]([OH:6])=[O:5])=[CH:15][CH:14]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 7732P-AnisidineHCID 83742-Chlorobenzoic AcidHCID 11430Potassium Carbonate

Product 1

HCID 2029182-[(4-Methoxyphenyl)amino]benzoic acidYield 76%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 52 g (0.33 mole) of 2-chlorobenzoic acid, 82 g (0.66 mole) of 4-methoxyaniline, 46 g (0.33 mole) of potassium carbonate, 5 g (0.025 mole) of cupric acetate and 150 ml of dimethylformamide was heated at reflux for two hours. The reaction mixture was cooled, 300 ml of water added and the mixture filtered. The filtrate was acidified with 50 ml of 6N hydrochloric acid, and the resulting solid was collected by filtration and recrystallized from acetonitrile to give 61 g of 2-(4-methoxyphenylamino)benzoic acid.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for two hours
  3. temperatureThe reaction mixture was cooled
  4. filtrationthe mixture filtered
  5. filtrationthe resulting solid was collected by filtration
  6. customrecrystallized from acetonitrile

Sources & evidence

ORD record
ord-e6d807f084a54bd7b8b146c779fc9dae
Source dataset
uspto-grants-1985_10
Patent number
US04549016

Linked notes

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