Ammonia → 8-Amino-1,2,3,4-tetrahydronaphthalen-2-ol

Participants

Reaction Conditions

Reaction Steps

To a solution of step-c product (23 g, 0.08 mol) in THF (253 ml, 11 times), tert-butanol (5.93 g (7.54 ml), 0.08 mol, 2.9 eq) was added. Condensed ammonia solution (3.9 ltrs, 170 times) was added (Condensed with the help of ammonia cylinder at −78° C. for 2 hrs). Sodium metal (5.51 g, 0.23 mol, 2.99 eq) was added portion wise (Reaction mixture colour changed during the addition sodium White-Blue—Disappearance of color) at −78° C. The overall reaction mass was stirred for 1.5 hrs at −78° C. and allowed to stir at RT for overnight. Progress of the reaction was monitored by TLC (20% ethyl acetate/hexane, Rf˜0.6). On completion of the reaction, (Total ammonia disappeared), reaction contents were diluted with water (100 ml) and the extracted with ethyl acetate (2×100 ml). Combined extract was dried over sodium sulfate, concentrated under reduced pressure and the crude obtained was purified by column chromatography (silica gel, 8% ethyl acetate/hexane) to yield the required product as a white solid (12 g, 53% yield).

Provenance & Evidence