Hydrochloric Acid → HCID 10710909, compound

Participants

Reaction Steps

Hydrogen chloride (1 mL, 4M in 1,4-dioxane) was added to a solution of (43) (0.1 g, 0.24 mmol) in 1,4-dioxane (5 mL) at 25° C. After 12 h, the reaction mixture was evaporated to a bright yellow solid residue which was basicified with NaOH(aq). The aqueous solution was extracted with EtOAc (3×50 mL). The combined organic layers were dried (Na2SO4), filtered, and concentrated in vacuo to give a yellow oily residue which was used in the next reaction without further purification (0.045 g, 59%): TLC (Rf =0.20; 15% MeOH/CH2Cl2); 1H NMR (CDCl3) δ 8.74 (s, 1H), 8.33 (d, 1H, J=5.4), 7.94 (d, 1H, J=8.8), 6.82 (d, 1H, J=8.8), 3.60 (m, 1H), 3.12 (d, 2H, J=11.3), 2.74 (t, 2H, J=11.7), 2.21 (s, 2H), 2.05 (d, 2H, J=12.5), 1.53 (s, 9H); 13C NMR (CDCl3) δ 164.2, 146.3, 136.2, 131.1, 129.4, 118.9, 113.4, 81.2, 49.8, 44.8, 32.9, 28.2; HRMS (FAB) m/z 322.1750 (M+H)+ (C16H23N3O4 requires 322.1761); Anal. (C16H23N3O4 ·1HCl·1CH3OH) C, H, N.

Provenance & Evidence