Sulfuric Acid → Methyl 6-aminopyridine-2-carboxylate

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Reaction Steps

H2SO4 (3.0 eq.) was added to a suspension of 6-aminopyridine-2-carboxylic acid in MeOH (0.3 M). The reaction mixture was heated to reflux for 20 h. After cooling down, the solvent was reduced in vacuo and the residue was added to cooled sat. aq. NaHCO3. The aqueous phase was extracted with DCM (2×) and the combined organic extracts were washed with brine and dried (Na2SO4). Evaporation of the solvent yielded the title compound as a white solid which was used in the next step without further purification. 1H NMR (400 MHz, DMSO-d6, 300K) δ 7.50 (1H, t, J=7.8 Hz), 7.18 (1H, d, J=7.3 Hz), 6.65 (1H, d, J=8.3 Hz), 6.28 (2H, bs), 3.79 (3H, s). MS (ES+) C7H8N2O2 requires: 152, found: 153 (M+H)+.

Provenance & Evidence