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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1904781Generated: November 2, 2026

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

https://huagongshe.com/reaction/1904781

Reaction equation

Participants

RoleNameHCIDCharge
Reactant3-Methyl-1-(4-nitrophenyl)-3-azabicyclo[3.1.0]hexane-2,4-dioneHCID 14068924—
CatalystPalladiumHCID 23938—
SolventEthanolHCID 702—
Product1-(4-Aminophenyl)-3-methyl-3-azabicyclo[3.1.0]hexane-2,4-dioneHCID 10171354—

Reaction Steps

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).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS04839379
Source datasetuspto-grants-1989_06
ORD IDord-0dedc1b6c3fd47a082cb9e635f19ec27
Source noteuspto-grants-1989_06