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

HRID 1416110Notes

Reaction equation

HRID 1416110 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.[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

4

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 2

HCID 23994ZincCatalystHCID 176Acetic AcidSolvent2×

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

Sources & evidence

ORD record
ord-2cdebc40ff094ccead1cec6f5653e852
Source dataset
uspto-grants-1999_06
Patent number
US05910495

Reaction notes

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