反应详情

Hydroxylamine hydrochloride (0.9 g) is added to a suspension, maintained at 0° C. with a bath of ice-cold water, of 2-(7-methoxy-1,8-naphthyridin-2-yl)-3-(5-methyl-2-oxohexyl)-1-isoindolinone (4.3 g) in a mixture (100 cc) of water and ethanol (50:50 by volume). The suspension obtained is allowed to return to a temperature in the region of 20° C. and a solution of sodium carbonate (0.7 g) in distilled water (10 cc) is added. The suspension obtained is heated to reflux for 22 hours. During this period, ethanol (80 cc) is added in two portions. Refluxing is maintained for 12 hours, adding in three portions further hydroxylamine hydrochloride (1.35 g) and sodium carbonate (1.05 g). The reaction mixture is then poured into water (1 litre). The aqueous phase is extracted with methylene chloride (3×300 cc). The organic phases are combined, washed with distilled water (2×100 cc), dried over magnesium sulphate, filtered and concentrated to dryness. After recrystallization in 2-propanol, 3-(2-hydroxyimino-5-methylhexyl)-2-(7-methoxy-1,8-naphthyridin-2-yl)-1-isoindolinone (1 g), m.p. 200° C., is obtained.

1. customThe suspension obtained
2. customto return to a temperature in the region of 20° C.
3. customThe suspension obtained
4. temperatureis heated
5. temperatureto reflux for 22 hours
6. waitDuring this period
7. temperatureRefluxing
8. temperatureis maintained for 12 hours
9. extractionThe aqueous phase is extracted with methylene chloride (3×300 cc)
10. washwashed with distilled water (2×100 cc)
11. dry with materialdried over magnesium sulphate
12. filtrationfiltered
13. concentrationconcentrated to dryness
14. customAfter recrystallization in 2-propanol