Oxalic Acid → HCID 86746511, compound

Participants

Reaction Steps

A mixture of 0.32 g of (1) (0.0014 mol) and 10 ml of thionyl chloride was heated to reflux for 1.5 h. The excess thionyl chloride was evaporated, the residue treated with ice-water and made basic with saturated aqueous K2CO3. The mixture was extracted 3× with 25 ml of CH2Cl2, the extracts washed with brine, dried, and the solvent evaporated. The residue was dissolved in 5 ml of methanol and added to 25 ml of methanol that had reacted with 0.35 g of Na (0.015 mol). The reaction was heated to reflux for 1.5 h. The solvent was evaporated, the residue was treated with ice-water and the mixture extracted 3× with 25 ml of CH2Cl2. The extracts were washed with brine, dried, and the solvent evaporated to give a dark liquid, 0.15 g. The liquid was dissolved in ethyl acetate and treated with oxalic acid to give 0.05 g of (2) after recrystallization from ethyl acetate, mp 150°-151° C. NMR ppm (D2O) 2.6-2.9 (2H, m), 3.1 (3H, s), 3.3 (1H, m), 3.65 (1H, m), 4.0 (3H, s), 4.05 (1H, dd), 4.35 (1H, d), 6.95 (1H, bs), 8.07 (1H, d), 8.1 (1H, d). Anal. C11H15N3O-C2H2O4 requires C: 52.88; H: 5.80; N: 14.23%. Found C: 52.66; H: 5.94; N: 14.04%.

Provenance & Evidence