Hydrochloric Acid → HCID 15444379, compound

Participants

Reaction Conditions

Reaction Steps

To a solution composed of 12.63 mL of 12 M hydrochloric acid in 6.32 mL ethanol was added 0.919 g (4.2 mmol) of compound 2. The solution was heated to reflux for 30 min and then cooled to 4° C. overnight. The resulting precipitate was removed by filtration and dissolved in a minimal volume of distilled water. The solution was neutralized by addition of 25% ammonium hydroxide and cooled at 4° C. for three hours. The resulting precipitate was removed by filtration and recrystallized from water to give a yellow compound (3) (0.484 g, 2.7 mmol) in 65% yield. mp 183-186° C. (lit: 183-184° C.). FTIR (KBr) (cm−1): 3420, 3340, 1690, 1635. 1H-NMR (DMSO-d6): δ (ppm) 6.95 (d, J=8.5 Hz, 1H), 6.56 (s, 1H), 6.49 (d, J=2.4 Hz, 1H), 6.46 (dd, J=10.0 Hz, J=2.6 Hz, 1H), 5.48 (bs, 2H), 5.00 (bs, 2H). 13C-NMR (DMSO-d6): δ (ppm) 159.95, 146.50, 141.19, 134.13, 123.04, 116.75, 113.70, 109.30, 108.42. HRMS expected: 177.05920; found: 177.05979.

Provenance & Evidence