Hydrazine hydrate (1:1) → 3-Amino-5-phenyl-1,3-dihydro-1,4-benzodiazepin-2-one

HRID 1769854Notes

Reaction equation

HRID 1769854 reaction equation
[C:1]1([C:7]2[C:13]3[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=3[NH:11][C:10](=[O:18])[CH:9]([N:19]3C(=O)C4=CC=CC=C4C3=O)[N:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.O.NN>O1CCCC1>[NH2:19][CH:9]1[N:8]=[C:7]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=2[NH:11][C:10]1=[O:18]

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 14800302(3RS)-1,3-dihydro-5-phenyl-3-phthalimido-2H-1,4-benzodiazepine-2-one

Product 1

HCID 42596493-Amino-5-phenyl-1,3-dihydro-1,4-benzodiazepin-2-oneYield 67.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of (3RS) -1,3-dihydro-5-phenyl-3-phthalimido-2H-1,4-benzodiazepine-2-one (8.2 g), hydrazine hydrate (1.08 g) and tetrahydrofuran (160 ml) was stirred for 1.0 hour at room temperature and heated under reflux for 1.5 hours. After the precipitates were filtered off, the filtrate was evaporated to small volume and the equivalent volume of diisopropyl ether was added thereto. The precipitates were collected by filtration to give (3RS)-1,3-dihydro-3-amino-5-phenyl-2H-1,4-benzodiazepine-2-one (3.64 g).

Workup

  1. temperatureheated
  2. temperatureunder reflux for 1.5 hours
  3. filtrationAfter the precipitates were filtered off
  4. customthe filtrate was evaporated to small volume
  5. additionthe equivalent volume of diisopropyl ether was added
  6. filtrationThe precipitates were collected by filtration

Sources & evidence

ORD record
ord-96c0b295945c48e1836ebcf65f9a236a
Source dataset
uspto-grants-1995_01
Patent number
US05382664

Reaction notes

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