反応 #351211

反応方程式

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

→

title compound

収率 102.2%

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

収率 102.2%

溶媒

acetic acid

acetic

反応条件

後処理

1. 1
   workup.ADDITIONadd (30 ml) over a fifteen minute period
2. 2
   workup.ADDITIONAfter complete addition
3. 3
   その他The zinc was separated by filtration
4. 4
   洗浄washed with ethyl acetate (75 ml)
5. 5
   濃縮The filtrate was concentrated in vacuo
6. 6
   その他partitioned between H2O (60 ml) and ethyl acetate (100 ml)
7. 7
   その他the phases separated
8. 8
   抽出The aqueous phase was extracted with ethyl acetate (2×75 ml)
9. 9
   乾燥dried with magnesium sulfate
10. 10
    ろ過filtered
11. 11
    濃縮concentrated in vacuo
12. 12
    その他to give a yellow oil which
13. 13
    その他was dried in vacuo

実験手順

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.

出典