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

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Reaction Steps

To a stirred mixture of 10 g of 1,2,3,4-tetrahydro-4-oxo-1-naphthylamine hydrochloride in 200 ml of dry tetrahydrofuran (THF) under a nitrogen atmosphere, 76 ml of triethylamine is added dropwise. The mixture is stirred for an additional 5 minutes, and 3 ml of methylisocyanate is added dropwise. The reaction mixture is stirred for 1 hour at room temperature and the solid collected. The filter cake is washed with THF and then with 3 × 50 ml of water. The THF filtrate is concentrated in vacuo to afford some product. The water-insoluble solid is air dried to afford 8.8 g of the title compound melting point 219°-221° C. Recrystallization from about 150 ml of methanol yeilds 7.4 g of the above product, melting point 220°-223° C.

Provenance & Evidence