N-Methyl-N'-(4-oxo-1,2,3,4-tetrahydronaphthalen-1-yl)urea → 1-Methyl-3-(1,2,3,4-tetrahydro-4-hydroxy-1-naphthyl)urea

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Reaction Steps

1-Methyl-3-(1,2,3,4-tetrahydro-4-oxo-1-naphthyl)-urea (3.3 g.) is hydrogenated in the presence of 0.3 g. of PtO2 10.05 mmole FeCl3 solution in 300 ml. of 95% ethanol using a low-pressure all-glass hydrogenator. After 615 ml. of hydrogen is absorbed, the excess hydrogen is removed by purging the system with nitrogen. The solution is filtered and evaporated to dryness in vacuo to afford 3.4 g. of an oil. The oil is stirred with about 20 ml. of acetone and the formed white solid is collected to afford 1.6 g. of the title compound as a cis/trans mixture, melting point 172°-180° C.

Provenance & Evidence