HCID 54493993, compound → 3-Amino-1-(4-methoxybenzyI)-5-phenyl-1,5-dihydrobenzo[b][1,4]diazepine-2,4-dione

HRID 264029Notes

Reaction equation

HRID 264029 reaction equation
[CH3:1][O:2][C:3]1[CH:36]=[CH:35][C:6]([CH2:7][N:8]2[C:14](=[O:15])[C:13](=[N:16]NC3C=CC=CC=3)[C:12](=[O:24])[N:11]([C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)[C:10]3[CH:31]=[CH:32][CH:33]=[CH:34][C:9]2=3)=[CH:5][CH:4]=1>C(O)(=O)C.CC(OCC1C2C(=CC=CC=2)C(COC(C)=O)=C2C=1C=CC=C2)=O.[Zn]>[NH2:16][CH:13]1[C:14](=[O:15])[N:8]([CH2:7][C:6]2[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:36][CH:35]=2)[C:9]2[CH:34]=[CH:33][CH:32]=[CH:31][C:10]=2[N:11]([C:25]2[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=2)[C:12]1=[O:24]

Participants

5

Reactant 1

HCID 54493993HCID 54493993, compound

Product 1

HCID 107389603-Amino-1-(4-methoxybenzyI)-5-phenyl-1,5-dihydrobenzo[b][1,4]diazepine-2,4-dioneYield 102.2%

Reagents, catalysts & solvents 3

HCID 23994ZincCatalystHCID 176Acetic AcidSolventHCID 613145Acetic acid 10-acetoxymethyl-anthracen-9-ylmethyl esterSolvent

Procedure

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.

Workup

  1. additionadd (30 ml) over a fifteen minute period
  2. additionAfter complete addition
  3. customThe zinc was separated by filtration
  4. washwashed with ethyl acetate (75 ml)
  5. concentrationThe filtrate was concentrated in vacuo
  6. custompartitioned between H2O (60 ml) and ethyl acetate (100 ml)
  7. customthe phases separated
  8. extractionThe aqueous phase was extracted with ethyl acetate (2×75 ml)
  9. dry with materialdried with magnesium sulfate
  10. filtrationfiltered
  11. concentrationconcentrated in vacuo
  12. customto give a yellow oil which
  13. customwas dried in vacuo

Sources & evidence

ORD record
ord-b4b47a42309c4638a9fdb71ec5050db7
Source dataset
uspto-grants-1997_07
Patent number
US05646140

Reaction notes

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