Reacción #351211

Ecuación de reacción

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

→

title compound

Rendimiento 102.2%

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

Rendimiento 102.2%

Disolventes

acetic acid

acetic

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.ADDITIONadd (30 ml) over a fifteen minute period
2. 2
   workup.ADDITIONAfter complete addition
3. 3
   OtroThe zinc was separated by filtration
4. 4
   Lavadowashed with ethyl acetate (75 ml)
5. 5
   ConcentraciónThe filtrate was concentrated in vacuo
6. 6
   Otropartitioned between H2O (60 ml) and ethyl acetate (100 ml)
7. 7
   Otrothe phases separated
8. 8
   ExtracciónThe aqueous phase was extracted with ethyl acetate (2×75 ml)
9. 9
   Secadodried with magnesium sulfate
10. 10
    Filtraciónfiltered
11. 11
    Concentraciónconcentrated in vacuo
12. 12
    Otroto give a yellow oil which
13. 13
    Otrowas dried in vacuo

Procedimiento

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.

Fuente