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

HRID 1904776Notes

Reaction equation

HRID 1904776 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10]23[CH2:15][CH:14]2[C:13](=[O:16])[NH:12][C:11]3=[O:17])=[CH:6][CH:5]=1)([O-])=O.[H][H]>C(O)C.[Pd]>[NH2:1][C:4]1[CH:5]=[CH:6][C:7]([C:10]23[CH2:15][CH:14]2[C:13](=[O:16])[NH:12][C:11]3=[O:17])=[CH:8][CH:9]=1

Participants

5

Reactant 2

HCID 128913411-(4-Nitrophenyl)-3-azabicyclo[3.1.0]hexane-2,4-dioneHCID 178418361HCID 178418361, compound

Product 1

HCID 140689341-(4-Aminophenyl)-3-azabicyclo[3.1.0]hexane-2,4-dione

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a solution of 25.9 g of 1-(4-nitrophenyl)-3-azabicyclo[3.1.0]hexane-2,4-dione (preparation as described in DE-OS 2 740 562) in 700 ml of ethanol are added 1.4 g of 5% palladium/carbon catalyst. Hydrogenation is carried out under normal pressure and at room temperature with hydrogen. When the absorption of hydrogen is complete (theoretical amount: 7500 ml), the reaction mixture is diluted with 1 ml of ethanol and concentrated after removal of the catalyst. The product so obtained is recrystallised from ethanol, affording the title compound with m.p. 183°-185° C.

Workup

  1. customWhen the absorption of hydrogen
  2. additionthe reaction mixture is diluted with 1 ml of ethanol
  3. concentrationconcentrated
  4. customafter removal of the catalyst
  5. customThe product so obtained
  6. customis recrystallised from ethanol

Sources & evidence

ORD record
ord-83a69b83f50b4471a82850bc1dcd28e4
Source dataset
uspto-grants-1989_06
Patent number
US04839379

Reaction notes

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