Reaction #3631

Reaction equation

9,10-dihydro-10-(4-nitrobenzoyl)-4H-furo[2,3-e]pyrrolo[1,2-a][1,4]diazepine

hydrazine

→

desired product

9,10-Dihydro-10-(4-aminobenzoyl)-4H-furo[2,3-e]pyrrolo[1,2-a][1,4]diazepine

Solvents

ethyl alcohol

Conditions

Workup

1. 1
   Temperatureheating
2. 2
   Temperatureunder reflux for 3 hours
3. 3
   OtherThe room temperature reaction mixture
4. 4
   Filtrationis filtered through diatomaceous earth
5. 5
   Concentrationthe filtrate concentrated in vacuo
6. 6
   workup.DISSOLUTIONThe residue is dissolved in methylene chloride
7. 7
   ConcentrationThe filtrate is concentrated in vacuo

Procedure

To a solution of 1 mmol of 9,10-dihydro-10-(4-nitrobenzoyl)-4H-furo[2,3-e]pyrrolo[1,2-a][1,4]diazepine in 20 ml of ethyl alcohol is added 0.2 g of 10% Pd/C and 2.5 mmol of hydrazine followed by stirring and heating under reflux for 3 hours. The room temperature reaction mixture is filtered through diatomaceous earth and the filtrate concentrated in vacuo. The residue is dissolved in methylene chloride and passed through a thin pad of hydrous magnesium silicate. The filtrate is concentrated in vacuo to give the desired product which is purified by flash chromatography on silica gel to give the desired product as a solid.

Source