Salicylic Acid → HCID 178484367, compound

Participants

Reaction Steps

N,N-Dimethylimidodicarbonimidic diamide (metformin free base) (1.66 g, 12.8 mmol) was dissolved in acetonitrile (45 mL) and the resulting solution was filtered through a medium frit to remove a small amount of sodium chloride that precipitated. To the filtrate was added dropwise at room temperature (over a 2 minute period) a solution of salicylic acid (1.42 g, 10.3 mmol) in acetonitrile (20 mL). The reaction solution became warm and a white solid precipitated about 1 minute after the addition was complete. After stirring for 1 h at room temperature, the mixture was chilled to 0° C. for 1 h. The white solid was filtered and the solid was washed with 20 mL ice-cold acetonitrile. The material was dried for 5 minutes on the frit followed by transfer of the solid to a round-bottom flask and the material was left under high vacuum overnight to yield 2.27 g (82%) of the title compound as a crystalline white solid. MP 152-154° C.; 1H NMR (400 MHz, MeOD) 7.82 (dd, J=7.67, 1.66 Hz, 1 H), 7.26 (m, 1 H), 6.76 (m, 2 H), 3.03 (s, 6 H); 13C NMR (101 MHz, MeOD) 176.31, 162.72, 161.33, 160.57, 133.87, 131.77, 120.38, 119.10, 117.25, 38.09; MS (ESI−) for C7H6O3 m/z 137.1 (M-H)−.

Provenance & Evidence