Acetic Acid → HCID 10358700, compound

Participants

Reaction Steps

A solution of (S)-2-(1-azabicyclo[2.2.2.]oct-3-yl)-2,3-dihydro-6-nitro-1H-benz[de]isoquinoline-1,3-dione (3.2 g; 8.8 mmol), prepared as in Example 2, in acetic acid (80 mL) was hydrogenated at atmospheric pressure over 10% Pd/C catalyst (1.2 g) for 3 hours. The catalyst was removed by filtration, the filtrate concentrated to a small volume, and the residue dissolved in water. This aqueous solution was added dropwise to dilute NH4OH and the solid that precipitated was collected on a Buechner funnel. Drying under vacuum gave (S)-6-amino-2-(1-azabicyclo[2.2.2]oct-3-yl)-2,3-dihydro-1H-benz[de]isoquinoline-1,3-dione (2.57 g; 7.93 mmol), m.p. 305°-308° C., [α]D25 -44.2° (c=0.373, MeOH).

Provenance & Evidence