HCID 12484293, compound → 2-Aminotetralin

Participants

Reaction Steps

Following the procedure of Example 27, but starting from 1-(2-acetamido-3-nitrophenoxy)-2,3-epoxypropane (5 g) and 2-aminotetralin (2.96 g) in absolute ethanol (80 ml), N-(1,2,3,4-tetrahydronaphth-2-yl)-2-hydroxy-3-(2-acetamido-3-nitrophenoxy)propanamine hydrochloride is obtained ((iA): R=H, E=acetamido, G=nitro, and the chain is attached to position 2 of the tetralin moiety) (Ex. 89). A mixture of N-(1,2,3,4-tetrahydronaphth-2-yl)-2-hydroxy-3-(2-acetamido-3-nitrophenoxy)propanamine hydrochloride (4 g) and 97% formic acid (19 ml) is charged in a hydrogenation vessel and freezed. The air contained in the reaction vessel is replaced by nitrogen and 10% Pd/C (0.25 g) is rapidly introduced therein. Hydrogenation is carried out at room temperature and 2.5 bar until the theoretical amount of hydrogen has been consumed. The reaction mixture is then heated, at atmospheric pressure, for 2 hours by means of a boiling water-bath. The catalyst is filtered off, the filtrate is evaporated to dryness and the obtained residue is taken up in hydrogen chloride saturated-isopropanol.

Provenance & Evidence