4-(1-Ethoxyethoxy)-3-methoxybenzonitrile → 1-[4-(1-Ethoxyethoxy)-3-methoxyphenyl]methanamine

Participants

Reaction Conditions

Reaction Steps

A solution of 5.0 g of 3-methoxy-4-(2-ethoxy-1-oxapropyl)benzonitrile in 25 ml anhydrous THF was added dropwise to 119.5 ml 1 M lithium aluminum hydride in THF. The mixture was refluxed for four hours, cooled to 0° C., and the excess reagent was quenched with 5 N NaOH. The precipitated aluminum salts were removed by filtration and the THF evaporated. The residue was partitioned between 200 ml ether and 75 ml H2O. The remaining ether layer was washed with 75 ml of brine, dried (K2CO3), filtered, and evaporated to yield 3.63 g of 2-methoxy-4-aminomethyl-(2-ethoxy-1-oxapropyl)benzene.

Provenance & Evidence