Water → HCID 67327786, compound

Participants

Reaction Steps

To stirred solution containing 240 mg (0.49 mmol) of 3-(benzyloxy)-6-(2,5-dimethyl-1H-pyrrol-1-yl)-2-(10-(methoxymethoxy)decyl)-4-methylpyridine in 10 mL of 9:1 ethanol-water were added 338 mg (4.87 mmol) of hydroxylamine hydrochloride followed by 273 mg (4.87 mmol) of potassium hydroxide. The reaction mixture was then stirred at reflux 6 h. then a second portion of 338 mg (4.87 mmol) of hydroxylamine hydrochloride followed by 273 mg (4.87 mmol) of potassium hydroxide was added and the mixture was stirred at reflux 16 h. The reaction mixture was then poured into 50 mL of water and extracted with two 50-mL portions of dichloromethane. The combined organic layer was washed with a 60-mL portion of brine, dried (MgSO4) and then concentrated under diminished pressure. The residue was purified by chromatography on a silica gel column (10×3 cm). Elution with 9:1 dichloromethane-methanol afforded the expected product as a yellowish oil: yield 113 mg (56%); silica gel TLC Rf 0.45 (9:1 dichloromethane-methanol); 1H NMR (CDCl3) δ 1.24-1.31 (br m, 12H), 1.63-1.53 (m, 4H), 2.16 (s, 3H), 2.62 (dd, 2H, J=8.0, 8.0 Hz), 3.28 (s, 3H), 3.48 (t, 2H, J=6.8 Hz), 4.59 (s, 2H), 4.71 (s, 2H), 5.24 (br s, 2H), 6.16 (s, 1H) and 7.31-7.43 (m, 5H); 13C NMR (CDCl3) δ 16.73, 29.19, 29.40, 29.46, 29.46, 29.48, 29.56, 29.72, 29.84, 32.24, 53.41, 67.85, 75.43, 96.34, 108.08, 127.73, 128.00, 128.00, 128.50, 128.50, 137.41, 142.46, 144.91, 153.46 and 154.13; mass spectrum (APCI), m/z 415.2957 (M+H)+ (C25H39N2O3 requires 415.2961).

Provenance & Evidence