Methyl Anthranilate → HCID 15084048, compound
Reaction equation
S(Cl)(Cl)=O.[C:5]([O:14][CH3:15])(=[O:13])[C:6]1[C:7](=[CH:9][CH:10]=[CH:11][CH:12]=1)[NH2:8].[C:16](=[O:19])([O-])[O-].[K+].[K+]>>[CH3:15][O:14][CH2:5][CH2:6][C:16]([NH:8][C:7]1[C:6](=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:5]([O:14][CH3:15])=[O:13])=[O:19]Participants
Procedure
To a suspension of 12.6 g (100 mmol) of the sodium salt obtained in the above (i) in 100 ml of benzene was dropwise added 8.0 ml (110 mmol) of thionyl chloride under stirring at room temperature for a period of 5 min. The mixture was then heated under reflux for 30 min. After chilling with ice, insolubles were removed by filtration. To the filtrate were added 15.1 g (100 mmol) of methyl anthranilate and 13.8 g (100 mmol) of potassium carbonate. The resulting mixture was then heated under reflux for 4 hrs. After the addition of ice water, the reaction mixture was washed sequentially with 6 N hydrochloric acid, saturated aqueous sodium hydrogencarbonate and saturated aqueous sodium chloride, and then was dried over anhydrous sodium sulfate. The solvent was distilled off to leave 8.8 g of an oily product. The oily product was crystallized from hexane to give 8.3 g of the desired compound as a pale yellow crystal.
Workup
- temperatureThe mixture was then heated
- temperatureunder reflux for 30 min
- temperatureAfter chilling with ice, insolubles
- customwere removed by filtration
- temperatureThe resulting mixture was then heated
- temperatureunder reflux for 4 hrs
- washthe reaction mixture was washed sequentially with 6 N hydrochloric acid, saturated aqueous sodium hydrogencarbonate and saturated aqueous sodium chloride
- dry with materialwas dried over anhydrous sodium sulfate
- distillationThe solvent was distilled off
Sources & evidence
- ORD record
- ord-faa94a97d1024c43a5985d926f5a40d8
- Source dataset
- uspto-grants-1992_02
- Patent number
- US05091403
Reaction notes
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