Ammonium Hydroxide → HCID 18415758, compound

Participants

Reaction Steps

5-Methoxy-11-aza-tricydo[7.3.1.02,7]trideca-2(7),3,5-triene hydrochloride (187 mg, 0.78 mmol) was brought to reflux in 48% HBr (5 mL). After 1 hour the solution was cooled and poured into aq. NH4OH soln., the pH was adjusted to ˜9 and the product was extracted with EtOAc (3×40 mL). The organic layer was washed with brine (50 mL), dried (MgSO4) and concentrated to a solid. (TLC 10% MeOH/CH2Cl2 (NH3) Rf 0.13). This material was dissolved in excess 1N HCl MeOH and concentrated. Recrystallization from MeOH/Et2O provided a solid (70 mg, 40%). 1H NMR (CD3OD) δ 6.99 (d, J=8.0 Hz, 1H), 8.83 (m, 2H), 3.48-3.11 (6H), 2.83 (d. J=18.0 Hz, 1H), 2.42 (br s, 1H), 2.08 (AB d, J=12.5 Hz, 1H), 1.93 (AB d, J=12.5 Hz, 1H). mp 295-298° C.

Provenance & Evidence