Hydrochloric Acid → HCID 22221627, compound

Participants

Reaction Conditions

Reaction Steps

To acid 23 (0.075 g, 0.250 mmole) was added pyridine-HCl (5.1 g, 43.3 mmole). After stirring at 200° C. for 30 minutes, the mixture was cooled to rt, poured into 2N HCl aq. and extracted with ethyl acetate. The combined organic phases were washed with saturated sodium bicarbonate, water, brine, and dried with magnesium sulfate. The organic phases were concentrated and the residue was loaded on to silica gel and chromatographed with silica gel (hexanes:ethyl acetate, 1:1) to afford 0.052 g (77%) of acid 24 as a white solid: Mp=260-262° C.; 1H NMR (DMSO-d6) δ 13.3 (br s,1 H), 9.79 (br s, 1 H), 9.46 (br s,1 H), 7.91 (d, 2 H, J=8.7 Hz), 7.30 (d, 1 H, J=2.4 Hz), 7.11 (s, 1 H), 7.08 (d, 1 H, J=2.4 Hz), 6.98 (d, 2 H, J=8.9 Hz); MS 269 (M−H)− Product was still contaminated with some 3-Cl compound.

Provenance & Evidence