Simple and convenient methods for synthesis, resolution and application of aminonaphthols

Abstract

Racemic aminonaphthols are obtained in 70-95% yield by simple and straightforward condensation of benzaldehyde, 2naphlhol and 1° or 2° amines in ethanol solvent under refluxing conditions. The racemic aminonaphthols 1-(αaminobcnzyl)-2-naphthol and 1-(α-pyrrolidinylbenzyl)-2-naphthol have been resolved using L -(+)-tartaric acid. The racemic l-(a-/V- butylaminobenzyl)-2-naphthol and l-(a-piperidylbenzyl)-2-naphthol have been resolved using fl-(+)-BINOL and boric acid. The racemic (2-methoxynaphth-1-yl) benzylamine is resolved using dibenzoyl-L-(-)-tartaric acid. The readiliy accessible chiral aminonaphthols are useful for resolution of important moieties like racemic BINOL, ibuprofen and mandclic acid.