2-Aminobenzyl alcohol → 2-Aminobenzaldehyde

Participants

Reaction Steps

2-Aminobenzyl alcohol (ex. Aldrich) (2 g) was oxidised with activated manganese dioxide (2.7 g) in chloroform over 20 hours. After filtration and concentration the crude product was purified by column chromatography on silica (ethyl acetate) to give 2-aminobenzaldehyde (1.9 g) as a dark-red oil which was used directly. The latter in xylene (70 ml) was heated under reflux in a Dean-Stark apparatus with ethyl cyanoacetate (3.7 g) (ex. Aldrich) and piperidine (0.8 ml). Upon cooling the 2-hydroxy-3-cyanoquinoline was collected by filtration, washed with ether, dried and converted to the 2-chloro-3-cyanoquinoline.

Provenance & Evidence