Back
HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1904776Generated: October 31, 2026

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

https://huagongshe.com/reaction/1904776

Reaction equation

Participants

RoleNameHCIDCharge
Reactant1-(4-Nitrophenyl)-3-azabicyclo[3.1.0]hexane-2,4-dioneHCID 12891341—
ReactantHCID 178418361HCID 178418361—
CatalystPalladiumHCID 23938—
SolventEthanolHCID 702—
Product1-(4-Aminophenyl)-3-azabicyclo[3.1.0]hexane-2,4-dioneHCID 14068934—

Reaction Steps

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.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS04839379
Source datasetuspto-grants-1989_06
ORD IDord-83a69b83f50b4471a82850bc1dcd28e4
Source noteuspto-grants-1989_06