反应详情

To a suspension of 5-nitro-2-amino-benzylamine hydrochloride (31 g, 0.152 mol) in dichloromethane (DCM) (450 ml) was added at 0° C. TEA (52.6 ml, 0.38 mol) and a solution of piperonyloyl chloride (27.3 g, 0.16 mol) in DCM (80 ml). The mixture was stirred for 2 hours at r.t. The solvent was removed under reduced pressure and the residue was triturated with ethanol/water 1/9 and then with diisopropyl ether. The obtained solid was dried in vacuum and suspended in toluene (900 ml) and POCl3 (670 ml). The mixture was heated at reflux for 2 hours and after the removal of solvent the residue was triturated with water/ammonia, washed with water and dried over P2O5. A mixture of the obtained solid and chloranile (32.7 g, 0.129 mol) in toluene (500 ml) was heated at reflux for 2 hours. The mixture was concentrated under reduced pressure and the residue was triturated with NaOH 1M, washed with water and with methanol. The obtained solid was dried in vacuum (37 g, 83% yield). C15H9N3O4, MW=295.26. mp: 220-222° C.

1. additionwas added at 0° C
2. customThe solvent was removed under reduced pressure
3. customthe residue was triturated with ethanol/water 1/9
4. customThe obtained solid was dried in vacuum
5. temperatureThe mixture was heated
6. temperatureat reflux for 2 hours
7. customafter the removal of solvent the residue
8. customwas triturated with water/ammonia
9. washwashed with water
10. dry with materialdried over P2O5
11. temperaturewas heated
12. temperatureat reflux for 2 hours
13. concentrationThe mixture was concentrated under reduced pressure
14. customthe residue was triturated with NaOH 1M
15. washwashed with water and with methanol
16. customThe obtained solid was dried in vacuum (37 g, 83% yield)