Sodium Bicarbonate → HCID 135555945, compound

Participants

Reaction Conditions

Reaction Steps

The product from Step D (1.90 g, 8.4 mmol) was dissolved in H2SO4/H2O (1:2, 60 mL) and cooled to 0° C. A solution of NaNO2 (0.64 g, 9.2 mmol) in H2O (2.0 mL) was added dropwise and the resultant dark solution was stirred for 2 h. Water (40 mL) was added to this solution and the mixture was heated to 110° C. for 2 h. After cooling the mixture to room temperature it was carefully neutralized with a saturated aqueous NaHCO3 solution and extracted with ethyl acetate (3×65 mL). The combined extracts were washed with brine (10 mL), dried (MgSO4) and evaporated to a residue which was purified by column chromatography (silica, 50% to 60% gradient of ethyl acetate in hexane) to give a solid (1.2 g, 83%): m.p: 153-155° C.; MS (ES) m/z 233(M+); 1H NMR (CDCl3) δ 9.39 (1H, s), 6.50 (1H, s), 6.34 (1H, s), 4.84 (1H, d, J=4.0 Hz), 4.00 (3H, m), 2.76 (2H, q, j=6.0 Hz), 2.01 (2H, m), 1.01 (3H, d, J=6.0 Hz).

Provenance & Evidence