Anthranilic Acid → HCID 19757772, compound

HRID 1587416Notes

Reaction equation

HRID 1587416 reaction equation
Cl[CH2:2][C:3]([NH:5][C:6]1[C:7](=[CH:11][CH:12]=[CH:13][CH:14]=1)[C:8]([OH:10])=[O:9])=[O:4].[C:15](O)(=O)[C:16]1[C:17](=[CH:19][CH:20]=[CH:21][CH:22]=1)N.NC1C=CC=C(C)C=1>CN(C)C=O>[CH3:15][C:16]1[CH:22]=[C:21]([CH2:2][C:3]([NH:5][C:6]2[C:7](=[CH:11][CH:12]=[CH:13][CH:14]=2)[C:8]([OH:10])=[O:9])=[O:4])[CH:20]=[CH:19][CH:17]=1

Participants

5

Reactant 3

HCID 227Anthranilic AcidHCID 7934m-ToluidineHCID 919916HCID 919916, compound

Product 1

HCID 19757772HCID 19757772, compoundYield 57%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

N(chloroacetyl)anthranilic acid 6.4 g (15 mmol) (synthesized from anthranilic acid by the same procedures as those of Example 9) and m-toluidine 9.5 ml (0.09 mol) were dissolved in 60 ml of dimethylformamide and heated at 80° to 90° C. for 4 hours. The reaction mixture was poured into ice water and extracted with ether. The resulting ether solution was extracted with 10% sodium hydroxide and the resulting aqueous solution was neutralized with 10% HCl solution. The neutralized solution was extracted with ether, and the ether solution was washed with water and dried. The solvent of dried solution was distilled off and the residue was recrystallized from benzene-hexane to obtain N[(3-methylphenyl)acetyl]anthranilic acid 4.7 g (yield: 57%).

Workup

  1. temperatureheated at 80° to 90° C. for 4 hours
  2. extractionextracted with ether
  3. extractionThe resulting ether solution was extracted with 10% sodium hydroxide
  4. extractionThe neutralized solution was extracted with ether
  5. washthe ether solution was washed with water
  6. customdried
  7. distillationThe solvent of dried solution was distilled off
  8. customthe residue was recrystallized from benzene-hexane

Sources & evidence

ORD record
ord-271598d7d86e43dfb17a0df6c582f175
Source dataset
uspto-grants-1993_06
Patent number
US05217961

Reaction notes

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