Tetrahydrofuran → Isopropanol hydrochloride

Participants

Reaction Conditions

Reaction Steps

To 2-((3-chlorophenyl)carbonyl)amino-5-nitroindane (2.2 g, 7.0 mmol) in THF (75 ml) was added BH3 ·THF (1.0M, 35 ml, 35 mmol) dropwise. The mixture was refluxed for 12 hr, cooled to 0° C., quenched with 4N HCl (60 ml), and refluxed for 1 hr. The resulting solution was evaporated to an oil, made basic with 50% NaOH, and extracted with methylene chloride (3×20 ml). The combined extracts were washed with water, dried over MgSO4, filtered and concentrated to an oil. Treatment with IPA/HCl yielded 2-((3-chlorophenyl)methyl)amino-6-nitroindane: (2.1 g, 88% two steps); m.p. 234°-237° C.

Provenance & Evidence