Hydrochloric Acid → HCID 68619468, compound

Participants

Reaction Steps

NaB(OAc)3H (6.4 g, 0.030 mol) was added in portions for 15 min to a mixture of pyrrolidine (2.1 mL, 0.025 mol) and 4-hydroxynaphthalene-1-carbaldehyde (3.40 g, 0.020 mol) in (C2H5)2O (80 mL) under vigorous stirring and cooling with an ice bath in an atmosphere of argon Ar. The mixture was stirred for 20 h and cooled with an ice bath. Concentrated HCl (18 mL) was added. The organic layer was separated and discarded. The aqueous one was alkalized with 10 N NaOH to pH 9 (30 mL) and extracted with (2×100 mL) (C2H5)2O. The combined extracts were dried with Na2SO4, and evaporated to give the title compound (5.1 g, 75%) was obtained as white crystals. LCMS-data: 228.1 and 229.1 (M+H)+, (calculated for C15H17NO 227.13). 1H NMR (400 MHz)-data (DMSO-d6, J, Hz): 9.18 (br s, 1H, OH); 6.83 (s, 2H, ArH); 3.79 (s, 3H, CH3); 3.44 (s, 2H, CH2Ar); 2.36-2.44 (m, 4H, CH2CH2CH2CH2,); 1.65-1.72 (m, 4H, CH2CH2CH2CH2,).

Provenance & Evidence