Chloroacetyl chloride → 2-(2-Chloroacetamido)-3-methylbenzoic acid
Reaction equation
[CH3:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:4]([C:5]([OH:7])=[O:6])[C:3]=1[NH2:11].[Cl:12][CH2:13][C:14](Cl)=[O:15]>C1C=CC=CC=1>[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:14](=[O:15])[CH2:13][Cl:12]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
3-Methylanthranilic acid 10 g (0.07 mol) was dissolved in dried benzene 100 ml. To this solution, chloroacetylchloride 5.81 ml (0.07 mol) was added dropwise at room temperature and heated under reflux for two hours. After cooling, deposited crystals were collected by filtration and recrystallized from benzene-toluene to obtain 3-methyl-N(chloroacetyl)anthranilic acid 11.7 g (yield: 79%).
Workup
- temperatureheated
- temperatureunder reflux for two hours
- temperatureAfter cooling
- filtrationdeposited crystals were collected by filtration
- customrecrystallized from benzene-toluene
Sources & evidence
- ORD record
- ord-2fd3153c55fa4a25989a38048270e672
- Source dataset
- uspto-grants-1993_06
- Patent number
- US05217961
Reaction notes
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