Ethanol → 5-(Hydroxymethyl)-2-[(propan-2-yl)amino]-1,2,3,4-tetrahydronaphthalene-1,6-diol

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Reaction Steps

In a mixture of 20 ml. ethanol and 2 ml. of triethylamine is dissolved 200 mg. of 6-hydroxy-5-hydroxymethyl-2-isopropylamino-3,4-dihydro-1(2H)-naphthalenone hydrochloride and, with the addition of 50 mg. of 5 % palladium-on-carbon, the solution is agitated in a current of hydrogen for 15 hours. The catalyst is filtered off and the filtrate is concentrated under reduced pressure. The resiude is dissolved in tetrahydrofuran. The insolubles are filtered off and the filtrate is concentrated under reduced pressure. The residue is recrystallized from ethanol-ethyl acetate. The procedure yields colorless crystals of 1,6-dihydroxy-5-hydroxymethyl-2-isopropylamino-1,2,3,4-tetrahydronaphthalene which is identical with the product according to the procedure of Example 71. Yield 108 mg.

Provenance & Evidence