m-Toluidine → HCID 19757757, compound

HRID 1587413Notes

Reaction equation

HRID 1587413 reaction equation
[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:12](=[O:15])[CH2:13]Cl.[CH3:16][C:17]1[CH:25]=[CH:24][CH:23]=[C:19](C(O)=O)[C:18]=1N.NC1C=CC=C(C)C=1>CN(C)C=O>[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:12](=[O:15])[CH2:13][C:19]1[CH:23]=[CH:24][CH:25]=[C:17]([CH3:16])[CH:18]=1

Participants

5

Reactant 3

HCID 7934m-ToluidineHCID 781012-Amino-3-methylbenzoic acidHCID 10775690131058-31-6

Product 1

HCID 19757757HCID 19757757, compoundYield 49%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
90 °C

Procedure

3-Methyl-N(chloroacetyl)anthranilic acid 7.5 g (33 mmol)(synthesized from 3-methylanthranilic acid by the same procedures as those of Example 9) and m-toluidine 11 ml (0.10 mol) were dissolved in 60 ml of dimethylformamide and heated at 90° C. for 4 hours. The reaction solution was poured into ice water and extracted with ether. The resulting ether solution was extracted with 10% sodium hydroxide and the resluting 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 was distilled off and the residue was recrystallized from benzene-toluene to obtain 3-methyl-N[(3-methylphenyl)acetyl]anthranilic acid 4.8 g (yield: 49%).

Workup

  1. extractionextracted with ether
  2. extractionThe resulting ether solution was extracted with 10% sodium hydroxide
  3. extractionThe neutralized solution was extracted with ether
  4. washthe ether solution was washed with water
  5. customdried
  6. distillationThe solvent was distilled off
  7. customthe residue was recrystallized from benzene-toluene

Sources & evidence

ORD record
ord-8c2fb22117424cc892f9f22c314f1529
Source dataset
uspto-grants-1993_06
Patent number
US05217961

Reaction notes

Loading…