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

HRID 1420015Notes

Reaction equation

HRID 1420015 reaction equation
[N+:1]([C:4]1[CH:24]=[CH:23][C:7]([C:8]([N:10]2[C:16]3[S:17][CH:18]=[CH:19][C:15]=3[CH2:14][N:13]3[CH:20]=[CH:21][CH:22]=[C:12]3[CH2:11]2)=[O:9])=[CH:6][CH:5]=1)([O-])=O.NN>C(O)C.[Pd]>[NH2:1][C:4]1[CH:24]=[CH:23][C:7]([C:8]([N:10]2[C:16]3[S:17][CH:18]=[CH:19][C:15]=3[CH2:14][N:13]3[CH:20]=[CH:21][CH:22]=[C:12]3[CH2:11]2)=[O:9])=[CH:6][CH:5]=1

Participants

5

Reactant 2

HCID 9321HydrazineHCID 218371519,10-Dihydro-10-(4-nitrobenzoyl)-4H-pyrrolo[1,2-a]thieno[2,3-e][1,4]diazepine

Product 1

HCID 218371419,10-Dihydro-10-(4-aminobenzoyl)-4H-pyrrolo[1,2-a]thieno[2,3-e][1,4]diazepine

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

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.

Workup

  1. temperatureheating
  2. temperatureunder reflux for 3 hours
  3. customThe cooled reaction mixture
  4. filtrationis filtered through diatomaceous earth
  5. concentrationThe filtrate is concentrated in vacuo to a residue which
  6. dissolutionis dissolved in methylene chloride
  7. concentrationThe filtrate is concentrated in vacuo

Sources & evidence

ORD record
ord-f5c107ee1a1145f3bfcfcd7514bb4780
Source dataset
uspto-grants-1999_03
Patent number
US05889001

Reaction notes

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