反应详情

A 5-L flask was set up with an overhead stirrer, temperature probe, and 500-mL addition funnel. The flask was charged with lithium aluminum hydride (100 g) and anhydrous tetrahydrofuran (1.5 L). The resulting suspension was treated with 4-amino-2-methyl-1H-isoindole-1,3(2H)-dione (100 g, 0.56 mol) at a rate such that the reaction did not become too vigorous. The resulting suspension was heated at reflux for 18 hours. The reaction vessel was cooled, placed in an ice bath, and cautiously quenched with 100 mL water, 100 mL 1N NaOH, and 300 mL water. The resulting suspension was treated with chloroform (1.5 L) and the pH of the suspension adjusted to 12 with 50% aqueous sodium hydroxide solution. The resulting suspension was treated with acetic anhydride (300 mL) while maintaining the pH at approximately 12. The reaction mixture was treated with sodium sulfate (800 g) and potassium carbonate (200 g), and the reaction mixture was filtered. The filter cake was washed with additional chloroform, and the combined filtrates were concentrated. The residue was crystallized from ethyl acetate to give 71 g (66%) of the desired product, mp 157° C.

1. customA 5-L flask was set up with an overhead stirrer
2. additiontemperature probe, and 500-mL addition funnel
3. temperatureThe resulting suspension was heated
4. temperatureat reflux for 18 hours
5. temperatureThe reaction vessel was cooled
6. customplaced in an ice bath
7. customcautiously quenched with 100 mL water, 100 mL 1N NaOH, and 300 mL water
8. additionThe resulting suspension was treated with chloroform (1.5 L)
9. additionThe resulting suspension was treated with acetic anhydride (300 mL)
10. temperaturewhile maintaining the pH at approximately 12
11. additionThe reaction mixture was treated with sodium sulfate (800 g) and potassium carbonate (200 g)
12. filtrationthe reaction mixture was filtered
13. washThe filter cake was washed with additional chloroform
14. concentrationthe combined filtrates were concentrated
15. customThe residue was crystallized from ethyl acetate