Triethylamine → HCID 67328261, compound

Participants

Reaction Steps

To stirred solution containing 1.22 g (2.26 mmol) of 2-(2,5-dimethyl-1H-pyrrol-1-yl)-5-benzyloxy-4-methyl-6-(10-benzyloxydecyl)-pyridine (17) in 40 mL of ethanol-water 4:1 were added 5.44 g (90.40 mmol) of hydroxylamine hydrochloride followed by 6.00 mL (45.20 mmol) of triethylamine. The reaction mixture was then stirred at reflux under argon atmosphere overnight. The reaction mixture was then poured into 100 mL of saturated aqueous NaHCO3 and extracted with two portions of 100 mL of dichloromethane. The combined organic solution was washed with a portion of 100 mL of brine, dried (MgSO4) and then concentrated under diminished pressure. The residue was purified by chromatography on a silica gel column. Elution with dichloromethane-methanol 9:1 gave the expected product as a yellowish oil: yield 722 mg (69%). 1H-NMR (CDCl3) δ 7.38-7.24 (m, 10H), 6.24 (s, 1H), 4.72 (s, 2H), 4.48 (s, 2H), 3.44 (t, 2H, J=8.0), 2.63 (t, 2H, J=8.0), 2.19 (s, 3H), 2.04 (s, 3H), 1.63-1.53 (m, 4H), 1.27 (m, 12H); 13C-NMR (CDCl3) δ 176.95, 153.85, 149.42, 146.90, 143.66, 138.66, 136.73, 128.62, 128.30, 127.77, 127.61, 127.44, 109.71, 75.86, 72.81, 70.50, 29.73, 29.58, 29.55, 29.52, 29.44, 29.42, 29.26, 26.16, 22.14, 16.73.

Provenance & Evidence