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

HRID 1456085Notes

Reaction equation

HRID 1456085 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-8016d66dcc1347999529cf923cb40263
Source dataset
uspto-grants-1998_12
Patent number
US05843944

Reaction notes

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