2-Methylbenzylamine → HCID 18957127, compound

Participants

Reaction Conditions

Reaction Steps

In a flame-dried, three-necked round-bottomed reaction flask equipped with reflux condenser, magnetic stirring bar and rubber septum, there was placed 1.0 g (0.0031 mole) of 4-chloro-3-(3-ethoxycarbonylpropionyl)-8-methoxyquinoline (the product of Preparation C) dissolved in 10 mL of dry tetrahydrofuran. Stirring was commenced and 0.8 mL (750 mg, 0.0062 mole) of 2-methylbenzylamine (available from the Aldrich Chemical Company, Inc. of Milwaukee, Wis.), was added over a two-minute period at room temperature (ca. 20° C.). The well-stirred reaction mixture was then heated to 60° C. and thereafter kept at that temperature for a period of approximately 16 hours (i.e., overnight). Upon completion of this step, the resulting reaction mixture was then filtered to remove 2-methylbenzylamine hydrochloride that had precipitated from the mixture and the filtrate was subsequently evaporated to near dryness while under reduced pressure to afford a crude solid product as the residue. The latter material was then purified by means of column chromatography over silica gel, using a 1% solution of diethylamine in ethyl acetate as the eluant. In this manner, there was ultimately obtained a 43 mg (3%) yield of pure 3-(3-ethoxycarbonylpropionyl)-8-methoxy-4-(2-methylbenzylamino)quinoline as the free base compound (isolated as a 0.25 hydrate), m.p. 152°-155° C. The pure product was further characterized by means of mass spectrum (MS) analysis and nuclear magnetic resonance (NMR) data, in addition to elemental analysis.

Provenance & Evidence