Ethanol → Ethyl 3-amino-5-chloropicolinate

Participants

Reaction Conditions

Reaction Steps

Absolute EtOH (1.00 mL, d=0.785, 17.0 mmol) and H2SO4 (96%, 0.10 mL, d=1.840, 1.8 mmol) were added to the hydrochloride salt of 3-amino-5-chloropicolinic acid (106) (0.100 g, 0.407 mmol). The mixture was stirred and heated to reflux. The mixture was refluxed (120° C.) for 19 h. The resulting solution was cooled to room temperature, poured over ice (1.0 g), and neutralized to pH 5 with solid Na2 CO3. The resulting mixture was extracted with EtOAc (4×3 mL), the organic layer dried (Na2SO4), and rota-evaporated to dryness, leaving the title compound as an orange solid, 68.6 mg (84.0%), mp 139.5°-142.5° C. (Lit., 165°-6° C., McCaustland and Cheng, J. Heterocycl. Chem. 7:467 (1970)); 1H NMR (CDCl3): δ1.44 (t, J=6.9 Hz, 3H), 4.45 (q, J=6.9 Hz, 3H), 5.84 (bs, 2H), 7.05 (d, J=1.5 Hz, 1H), 7.99 (d, J=1.8 Hz, 1H).

Provenance & Evidence