N,N-dimethylhydroxylamine hydrochloride → HCID 18958982, compound

Participants

Reaction Steps

To a solution of 3-cyclohexyl-2-[4-(quinolin-2-yl-methoxy)phenyl]-propionic acid (389 mg, 1 mmol) in methylene chloride (10 mL) was added 1,1'-carbonyldiimidazole (162 mg, 1 mmol). The mixture was stirred at ambient temperature for 15 minutes and then N,N-dimethylhydroxylamine hydrochloride (147 mg, 1.5 mmol) was added. The resulting mixture was stirred at ambient temperature for an additional 20 minutes and then partitioned between ethyl acetate (50 mL) and saturated NaHCO3 (5 mL). The organic layer was washed with water and brine, dried over MgSO4 and concentrated in vacuo. Purification on a silica gel column eluting with 2:1 CH2Cl2 -EtOAc afforded 370 mg (86%) of the title compound. m.p. 98°-99° C. 1H NMR (DMSO-d6, 300 MHz) δ 0.9 (m, 2H), 1.1 (m, 4H), 1.63 (m, 6H), 1.8 m (m, 1H), 2.6 (s, 6H), 3.7 (t, J=7Hz, 1H), 5.35 (s, 2H), 7.04 (d, J=9Hz, 2H), 7.23 (d, J=9Hz, 2H), 7.62 (m, 1H), 7.68 (d, J =8Hz, 1H), 7.8 (m, 1H), 8.0 (t, J=8Hz, 2H), 8.42 (d, J=8Hz, 1H). IR (CDCl3): 1750,1600 cm-1. MS (DCI/NH3) m/e 433 (M+H)+. Analysis calcd for C27H32N2O3 : C, 74.97; H, 7.46; N, 6.48. Found: C, 74.81; H, 7.47; N, 6.41.

Provenance & Evidence