反应详情

A mixture of 5.2 g (0.027 mol) of (±)-4-(2-hydroxyethyl)-3,4-dihydro-2(1H)-quinolinone, 15 g (0.126 mol) of thionyl chloride, 200 ml of dry chloroform and 10 drops of pyridine is heated to reflux for 4 h. After the mixture is cooled, 50 ml of water are added dropwise and the mixture is stirred for 30 minutes. The organic phase is separated after settling has taken place, dried over magnesium sulphate and concentrated under vacuum. The residue is chromatographed on a silica column. Elution with a dichloromethane/acetone (90:10) mixture yields an oil which is crystallized in cyclohexane. 5 g (88%) of (±)-4-(2-chloroethyl)-3,4-dihydro-2(1H)-quinolinone, melting point 112°-113° C., are obtained.

1. temperatureis heated
2. temperatureto reflux for 4 h
3. temperatureAfter the mixture is cooled
4. customThe organic phase is separated after settling
5. dry with materialdried over magnesium sulphate
6. concentrationconcentrated under vacuum
7. customThe residue is chromatographed on a silica column
8. washElution with a dichloromethane/acetone (90:10) mixture
9. customyields an oil which
10. customis crystallized in cyclohexane