Hydrochloric Acid → HCID 68864584, compound

Participants

Reaction Steps

A mixture of 2-amino-5-nitrobenzoic acid (151 mg, 0.77 mmol) in dichloromethane (2.0 mL) was treated with chlorotrimethylsilane (1.70 mL of 1M solution in CH2Cl2, 1.70 mmol) and pyridine (2.0 mL), stirred at room temperature for 30 minutes, treated with benzenesulfonyl chloride (150 μL, 1.16 mmol), stirred overnight at room temperature, warmed to 40° C., stirred overnight, treated with 1N HCl (2.0 mL), and extracted with dichloromethane (2×). The combined extracts were washed with distilled water and brine, dried (MgSO4), filtered, and concentrated. The resulting residue was purified by preparative HPLC to provide the desired product. MS (ESI(−)) m/e 335 (M−H)−; 1H NMR (300 MHz, DMSO-d6) δ 10.96 (s, 1H), 8.58 (d, 1H), 8.39 (dd, 1H), 7.96 (m, 2H), 7.74-7.60 (m, 4H), 3.91 (s, 3H).

Provenance & Evidence