Trans-3-azido-1,2,3,4-tetrahydro-5-methoxy-2-naphthalinol → Trans-3-amino-1,2,3,4-tetrahydro-5-methoxy-2-naphthalinol

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Reaction Steps

4.0 g of palladium on charcoal (10%) are coated with 100 ml of ethanol. 8.76 g (0.040M) of trans-3-azido-1,2,3,4-tetrahydro-5-methoxy-2-naphthalinol are dissolved in 100 ml of ethanol, and the solution is added to the catalyst suspension. The mixture is subsequently hydrogenated at 20° at 1.2 bar hydrogen pressure. Every 10 minutes for 50 minutes, the reaction vessel is emptied and rinsed with hydrogen. The reaction mixture is then filtered through a G 4 Hyflo suction filter. The catalyst is washed with methylene chloride and the filtrate concentrated by evaporation. Trans-3-amino-1,2,3,4-tetrahydro-5-methoxy-2-naphthalinol is obtained (m.p. 130°-132° after purification by column chromatography, silica gel, methylene chloride and 10% methanol).

Provenance & Evidence