Reaction #3641

Reaction equation

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

hydrazine

→

desired product

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

Solvents

ethyl alcohol

Conditions

Workup

1. 1
   Temperatureheating
2. 2
   Temperatureunder reflux for 3 hours
3. 3
   OtherThe cooled reaction mixture
4. 4
   Filtrationis filtered through diatomaceous earth
5. 5
   ConcentrationThe filtrate is concentrated in vacuo to a residue which
6. 6
   workup.DISSOLUTIONis dissolved in methylene chloride
7. 7
   ConcentrationThe filtrate is concentrated in vacuo

Procedure

To a solution of 5 mmol of 9,10-dihydro-10-(4-nitrobenzoyl)-4H-pyrrolo-[1,2-a]thieno[2,3-e][1,4]diazepine in 25 ml of ethyl alcohol is added 0.13 g of 10% Pd/C and 15 mmol of hydrazine followed by stirring and heating under reflux for 3 hours. The cooled 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 on silica gel to give the desired product as a solid.

Source