3-Methyl-1-(4-nitrophenyl)-3-azabicyclo[3.1.0]hexane-2,4-dione → 1-(4-Aminophenyl)-3-methyl-3-azabicyclo[3.1.0]hexane-2,4-dione

HRID 1904781Notes

Reaction equation

HRID 1904781 reaction equation
[CH3:1][N:2]1[C:7](=[O:8])[CH:6]2[C:4]([C:9]3[CH:14]=[CH:13][C:12]([N+:15]([O-])=O)=[CH:11][CH:10]=3)([CH2:5]2)[C:3]1=[O:18]>C(O)C.[Pd]>[NH2:15][C:12]1[CH:11]=[CH:10][C:9]([C:4]23[CH2:5][CH:6]2[C:7](=[O:8])[N:2]([CH3:1])[C:3]3=[O:18])=[CH:14][CH:13]=1

Participants

4

Reactant 1

HCID 140689243-Methyl-1-(4-nitrophenyl)-3-azabicyclo[3.1.0]hexane-2,4-dione

Product 1

HCID 101713541-(4-Aminophenyl)-3-methyl-3-azabicyclo[3.1.0]hexane-2,4-dione

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution of 1.5 g of 3-methyl-1-(4-nitrophenyl)-3-azabicyclo[3.1.0]hexane-2,4-dione in 50 ml of ethanol is hydrogenated in the presence of 0.1 g of 5% palladium on carbon. When the hydrogenation is complete, the catalyst is removed and the filtrate is concentrated and the residue is recrystallised from ethyl acetate/petroleum ether. The title compound is obtained in the form of pale pink crystals with m.p. 137°-139° C. and Rf=0.47 on thin-layer silica gel plates in the system methylene chloride/methanol (15:1).

Workup

  1. customthe catalyst is removed
  2. concentrationthe filtrate is concentrated
  3. customthe residue is recrystallised from ethyl acetate/petroleum ether

Sources & evidence

ORD record
ord-0dedc1b6c3fd47a082cb9e635f19ec27
Source dataset
uspto-grants-1989_06
Patent number
US04839379

Reaction notes

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