Acetic Acid → Isopropanol hydrochloride

Participants

Reaction Conditions

Reaction Steps

7-Nitro-3,4-dihydro-2(1H)-naphthaleneone (1.50 g, 7.85 mmol), 3-chlorobenzylamine (4.70 ml, 39.3 mmol), acetic acid (6.0 ml), 4 Å molecular sieves (20 ml), THF (15 ml), and MeOH (15 ml) were introduced into a flask and cooled to 0° C. Sodium cyanoborohydride (0.99 g, 15.7 mmol) was added portionwise over a 5-minute period. The mixture was stirred for 14 hr, filtered through celite, and concentrated to a syrup. The mixture was made basic with 2N NaOH and extracted with ether (3×50 ml). The combined extracts were washed with water, dried over magnesium sulfate, filtered, concentrated and chromatographed over silica gel (3% methanol/methylene chloride). Treatment of the oil with IPA/HCl yielded 7-nitro-2-(((3-chlorophenyl)methyl)amino)-1,2,3,4-tetrahydronaphthalene hydrochloride: (1.34 g, 50%); M.S. (M+H)+ =317.

Provenance & Evidence