反应详情

11.8 g (55.6 mmol) 1-[1-(isopropylthio)methyl]-2-nitrobenzene (VII-2) in 150 ml methanol are placed in a 500 ml three-necked flask equipped with a stirrer and thermometer, mixed with 150 ml concentrated hydrochloric acid with stirring, and 17.6 g powdered tin (148.5 mmol) are added in portions at 20-40° C. Stirring of the mixture wird is continued at 40° C. for about an hour. The reaction is cooled, filtered and mixed with 1300 ml of an ice-cooled 10% sodium hydroxide solution. Then it is extracted twice with dichloromethane, dried over sodium sulfate, and the solvent is evaporated under vacuum. The crude product is purified on silica gel with 3:1 hexane/methyl t-butyl ether. 4.6 g (94.6% purity by HPLC, 43.2% theoretical yield) of 2-[1-(isopropylthio)methyl]aniline are obtained as a yellow oil [logP (pH 2.3)=1.94].

1. customequipped with a stirrer
2. stirringStirring of the mixture wird
3. waitis continued at 40° C. for about an hour
4. temperatureThe reaction is cooled
5. filtrationfiltered
6. additionmixed with 1300 ml of an ice-
7. temperaturecooled 10% sodium hydroxide solution
8. extractionThen it is extracted twice with dichloromethane
9. dry with materialdried over sodium sulfate
10. customthe solvent is evaporated under vacuum
11. customThe crude product is purified on silica gel with 3:1 hexane/methyl t-butyl ether