O-Phenylenediamine → HCID 10729798, compound

Participants

Reaction Steps

1,2-Phenylenediamine (5 g) was added to a solution of 1-adamantanecarboxaldehyde (7.6 g) in methanol (100 ml). The solution was stirred at 23° for 2 h, then sodium borohydride (3.5 g) was added portionwise. The resulting mixture was stirred at 230 for 2 h, then diluted with ethyl acetate (400 ml) and filtered. The organic layer was washed with brine (300 ml), dried and concentrated in vacuo to a residue, which was taken up in ethyl ether and the inorganic salts still present were removed by filtration. The filtrate was concentrated in vacuo and purified by flash chromatography to give the title compound as a beige solid (1.2 g). M.p.86°-7° T.l.c. CH-EA (7:3), Rf 0.6.

Provenance & Evidence