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

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of 8-amino-2-naphthol (40 g, 0.25 mol) in THF (800 ml, 20 times), Boc anhydride (54.8 g (57.7 ml), 0.25 mol, 1 eq) was added at rt. The overall reaction mass was heated to 70° C. and maintained for 24 hrs at the same temperature. Progress of the reaction was monitored by TLC (20% ethyl acetate/hexane, Rf˜0.6). On completion of the reaction, solvent was distilled off completely and the residue obtained was taken in ethyl acetate (200 ml). Organic layer was washed with saturated sodium carbonate solution (2×200 ml) followed by with water (2×200 ml), dried the contents over sodium sulfate and concentrated under reduced pressure. The crude obtained was taken in diisopropyl ether (150 ml), stirred for 15 min and filtered. Solid obtained was washed with diisopropyl ether again and dried to yield the required product as an off white solid (49 g, 75% yield).

Provenance & Evidence