Реакция #351211

Уравнение реакции

1 -(4-Methoxybenzyl)-5-phenyl-3-(phenylhydrazono)-1,5-dihydrobenzo [b] [1, 4] diazepine-2, 4-dione

→

title compound

Выход 102.2%

3-Amino-1-(4-methoxybenzyI)-5-phenyl-1,5-dihydrobenzo[b][1,4]diazepine-2,4-dione

Выход 102.2%

Растворители

acetic acid

acetic

Условия реакции

Обработка

1. 1
   workup.ADDITIONadd (30 ml) over a fifteen minute period
2. 2
   workup.ADDITIONAfter complete addition
3. 3
   ДругоеThe zinc was separated by filtration
4. 4
   Промывкаwashed with ethyl acetate (75 ml)
5. 5
   КонцентрированиеThe filtrate was concentrated in vacuo
6. 6
   Другоеpartitioned between H2O (60 ml) and ethyl acetate (100 ml)
7. 7
   Другоеthe phases separated
8. 8
   ЭкстракцияThe aqueous phase was extracted with ethyl acetate (2×75 ml)
9. 9
   Сушкаdried with magnesium sulfate
10. 10
    Фильтрацияfiltered
11. 11
    Концентрированиеconcentrated in vacuo
12. 12
    Другоеto give a yellow oil which
13. 13
    Другоеwas dried in vacuo

Методика

To a vigorously stirred slurry of zinc dust (6.49 g) in acetic acid (50 ml) cooled to 10° C., was added a slurry of 1 -(4-Methoxybenzyl)-5-phenyl-3-(phenylhydrazono)-1,5-dihydrobenzo [b] [1, 4] diazepine-2, 4-dione (5.75 g,12.1 mmol) in acetic add (30 ml) over a fifteen minute period. After complete addition, the solution was warmed to room temperature and stirred three hours. The zinc was separated by filtration and washed with ethyl acetate (75 ml). The filtrate was concentrated in vacuo and partitioned between H2O (60 ml) and ethyl acetate (100 ml). The pH was adjusted to 9 with saturated aqueous sodium carbonate and the phases separated. The aqueous phase was extracted with ethyl acetate (2×75 ml), the organic layers combined, dried with magnesium sulfate, filtered and concentrated in vacuo to give a yellow oil which was dried in vacuo to give the title compound (4.79 g) NMR (300 MHz, CDCl3): d 3.05 (s, 2H), 3.75 (s, 3H), 4.35 (s, 1H), 4.64 (d, J=14.7 Hz, 1H), 5.82 (d, J=14.7 Hz, 1H), 6.59-6.85 (m, 6H), 7.06-7.29 (m, 6H), 7.51(d, J=7.4 Hz. 1H); MS (FAB): m/z=388.2 (MH+); TLC (CH2Cl2 /CH3OH (9:1)): Rf =0.50.

Источник