Chloroacetyl chloride → 131058-31-6

HRID 1587412Notes

Reaction equation

HRID 1587412 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

HCID 6577Chloroacetyl chlorideHCID 781012-Amino-3-methylbenzoic acid

Product 1

HCID 10775690131058-31-6Yield 79%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

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

  1. temperatureheated
  2. temperatureunder reflux for two hours
  3. temperatureAfter cooling
  4. filtrationdeposited crystals were collected by filtration
  5. 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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