Hydrochloric Acid → HCID 20742869, compound

Participants

Reaction Steps

A solution of 16 (417 mg, 1.5 mmol) in a mixture of methanol (25 mL), water (5 mL) and conc. HCl (2.5 mL) was heated under reflux for 4 h. The solution was diluted with water (7 mL) and extracted with EtOAc. The combined organic phases were washed with brine, dried and evaporated to give a viscous oil. Trituration with ether and recrystallization (Et2O-hexanes) afforded 12 as red microcrystals (255 mg, 72%), mp 113-115° C.; UV: λmax (EtOH)/nm 246 (ε/M−1cm−1 16 600), 431 (5600); λmax [EtOH-25 mM Na phosphate, pH 7.0 (1:40)]/nm 238 (ε/M−1cm−1 16 400), 289 (6060), 450 (5060); IR: νmax/cm−1 3420, 3380, 1740, 1645, 1600, 1520; 1H NMR: δH (90 MHz) 7.64 (br s, 1H), 7.16 (br s, 1H), 6.71 (br s, 1H), 3.87 (t, J=8.3 Hz, 2H), 3.69 (s, 3H), 3.51 (s, 2H) and 3.15 (t, J=8.3 Hz, 2H). Anal. Calcd for C11H12N2O4: C, 55.93; H, 5.12; N, 11.85. Found: C, 55.74; H, 5.07; N, 11.68.

Provenance & Evidence