Reaction #3620

Reaction equation

10,11-dihydro-10-(4-nitrobenzoyl)-5H-imidazo[2,1-c][1,4]benzodiazepine

hydrazine

→

desired product

10,11-Dihydro-10-(4-aminobenzoyl)-5H-imidazo[2,1-c][1,4]benzodiazepine

Solvents

ethyl alcohol

Conditions

Workup

1. 1
   Temperatureheating
2. 2
   Temperatureunder reflux for 3 hours
3. 3
   FiltrationThe reaction mixture is filtered through diatomaceous earth
4. 4
   ConcentrationThe filtrate is concentrated in vacuo to a residue which
5. 5
   workup.DISSOLUTIONis dissolved in methylene chloride
6. 6
   ConcentrationThe filtrate is concentrated in vacuo

Procedure

To a solution of 5 mmol of 10,11-dihydro-10-(4-nitrobenzoyl)-5H-imidazo[2,1-c][1,4]benzodiazepine in 100 ml of ethyl alcohol is added 0.5 g of 10% Pd/C and 10 mmol of hydrazine followed by stirring and heating under reflux for 3 hours. The reaction mixture is filtered through diatomaceous earth. The filtrate is concentrated in vacuo to a residue which is dissolved in methylene chloride and passed through a pad of hydrous magnesium silicate. The filtrate is concentrated in vacuo to give the desired product which is purified by flash chromatography to give the desired product as a solid.

Source