Hydrazine → 4,5-Dihydro-5-(4-aminobenzoyl)pyrrolo[1,2-a]quinoxaline

HRID 1598193Notes

Reaction equation

HRID 1598193 reaction equation
[N+:1]([C:4]1[CH:24]=[CH:23][C:7]([C:8]([N:10]2[C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[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:5]=[CH:6][C:7]([C:8]([N:10]2[C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[N:13]3[CH:20]=[CH:21][CH:22]=[C:12]3[CH2:11]2)=[O:9])=[CH:23][CH:24]=1

Participants

5

Reactant 2

HCID 9321HydrazineHCID 218371354,5-Dihydro-5-(4-nitrobenzoyl)pyrrolo[1,2-a]quinoxaline

Product 1

HCID 218370054,5-Dihydro-5-(4-aminobenzoyl)pyrrolo[1,2-a]quinoxaline

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a solution of 1 mmol of 4,5-dihydro-5-(4-nitrobenzoyl)pyrrolo[1,2-a]quinoxaline 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 2 hours. The hot reaction mixture is filtered through diatomaceous earth and the filter cake washed with hot chloroform and the filtrate concentrated in vacuo. The residue is triturated with ethyl acetate and the mixture filtered to give the desired product as crystals, m.p. 225°-228° C.

Workup

  1. temperatureheating
  2. temperatureunder reflux for 2 hours
  3. filtrationThe hot reaction mixture is filtered through diatomaceous earth
  4. washthe filter cake washed with hot chloroform
  5. concentrationthe filtrate concentrated in vacuo
  6. customThe residue is triturated with ethyl acetate
  7. filtrationthe mixture filtered

Sources & evidence

ORD record
ord-1538368544234e46828e1e9700905db5
Source dataset
uspto-grants-1998_04
Patent number
US05736540

Reaction notes

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