Phenol → 11-Phenoxy-1,2,4,5-tetrahydro-3-azepino[4,5-b]quinoline-carboxylic acid ethyl ester

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Reaction Steps

A mixture of 15.0 gm (49.4 millimols) of 11-chloro-1,2,4,5-tetrahydro-3-azepino[4,5-b]quinoline-carboxylic acid ethyl ester and 28.2 gm (300 millimols) of phenol was melted at 150° C and held at that temperature for 40 hours. Then, the mixture was taken up in ethyl acetate, and the solution was extracted with dilute sodium hydroxide. The ethyl acetate phases were evaporated and chromatographed on a silicagel column with toluene/acetone (8:1) as the eluant. Subsequently, the crystals were triturated with ether/petroleum ether.

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