Hydrochloric Acid → HCID 16215363, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 2-chloro-4-nitrobenzoic acid (3 g, 14.88 mmol) in DMF (40 mL) was added 3-3′-acetamidolphenol (2.47 g, 16.38 mmol), potassium carbonate (3.08 g, 16.38 mmol), and copper powder (102 mg, 1.61 mmol). After heating at 130° C. overnight, the reaction mixture was cooled to room temperature and poured to ice-1 N HCl solution (300 mL) slowly. The solution was stirred until the brown solid was formed. The solid was filtered off and washed with cold water to yield a brown solid (3.1 g). A crude solid was dissolved in conc. sulfuric acid (20 mL) and heated at 80° C. for 1 hour. After cooling to room temperature, the reaction mixture was poured to ice (350 mL volume) and stirred for 1 hour. The precipitated solid was filtered off and re-suspended in 2.5% aq. sodium carbonate solution. The solid was filtered and washed with cold water and dried under vacuum. The solid was further recrystallized in pyridine or pyridine/water to yield 1.23 g of S3 (Y═O) (60%, two steps) as a yellowish-brown solid. 1H-NMR (DMSO-d6) δ 8.37 (d, J=2.0, 1H), 8.32 (d, J=8.4, 1H), 8.15 (dd, J=2.0, 8.4, 1H), 7.88 (d, J=8.8, 1H), 6.75 (bs, 2H), 6.72 (dd, J=2.0, 8.8, 1H), 6.56 (d, J=2.0, 1H). ESI-MS m/z (H+H) calc'd: 257.2, found 257.1.

Provenance & Evidence