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

HRID 1980483Notes

Reaction equation

HRID 1980483 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-7cc6081060d24fc8967205f00a90561c
Source dataset
uspto-grants-1985_04
Patent number
US04510139

Reaction notes

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