p-Toluidine → Benzoic acid, 2-[[[(4-methylphenyl)amino]acetyl]amino]-

HRID 1587415Notes

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].[NH2:15][C:16]1[CH:21]=[CH:20][C:19]([CH3:22])=[CH:18][CH:17]=1>CN(C)C=O>[CH3:22][C:19]1[CH:20]=[CH:21][C:16]([NH:15][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:17][CH:18]=1

Participants

Conditions

Temperature: 90 °C

Procedure

N(chloroacetyl)anthranilic acid 3.2 g (0.02 mol) and p-toluidine 3.4 g (0.005 mol) were dissolved in 4 ml of dimethylformamide and heated at 90° C. for 3 hours. The reaction solution was poured into ice water and deposited crystals were collected by filtration. These crystals were washed with ether and recrystallized from ethanol to obtain N-[(4-methylphenylamino)acetyl]anthranilic acid 2.6 g (yield: 70%).

Workup

filtrationwere collected by filtration
washThese crystals were washed with ether
customrecrystallized from ethanol

Sources & evidence

ORD record: ord-61fdc2c96d8a46b6b9de31e9a02cc708
Source dataset: uspto-grants-1993_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05217961

Reaction notes

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