1-Iodopropane → HCID 21298232, compound

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Reaction Steps

A solution of 4,5-dihydrooxazolo[5,4-f]quinolin-2-amine, 5.0 g (26.7 mmol), (Example 27), in 200 ml of acetonitrile is refluxed with 1-iodopropane, 10.2 g (60 mmol), for 24 hours. The volatiles are then removed in-vacuo and the resulting solid is washed with diethyl ether and dried. The resulting 2-amino-4,5-dihydrooxazolo[5,4-f]quinolinium iodide is dissolved in 150 ml of water and treated with sodium borohydride, 1.7 g (50 mmol), in small portions. The mixture is stirred at room temperature for 2 hours. Following acidification with 10% hydrochloric acid, the mixture is stirred for another hour. The volatile components are removed in-vacuo and the residue is partitioned between chloroform and 1% ammonium hydroxide. The organic extract is concentrated and purified by column chromatography to give (±) 4,5,5a,6,7,8-hexahydro-6-propyloxazolo [5,4-f]quinolin-2-amine.

Provenance & Evidence