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With water; iron; ammonium chloride In ethanol at 80℃; for 4h;
5.4 Step 4: methyl 3-amino-6-methoxy picolinate
A mixture of methyl 6-methoxy-3-nitro-picolinate (1.03 g, 4.8 mmol), iron powder (1.08 g, 19 mmol), ammonium chloride (389 mg, 7.3 mmol) and ethanol / water (50 mL, 4:1) was stirred at 80 °C for 4 h. After cooled, the mixture was filtered, and the resulting filtrate was poured into water and extracted with ethyl acetate. The organic layer was washed with water, dried, and concentrated under vacuum. The resulting residue was purified by column chromatography to give the title compound (420 mg, 48 %). 1H NMR (CDCl3): δ 7.05 (1H, d, J = 8.8 Hz), 6.81 (1H, d, J = 8.8 Hz), 5.46 (2H, br), 3.94 (3H, s), 3.92 (3H, s).
48%
With iron; ammonium chloride In ethanol; water at 80℃; for 4h;
5.4 methyl 3-amino-6-methoxy picolinate
A mixture of methyl 6-methoxy-3-nitro-picolinate (1.03 g, 4.8 mmol), iron powder (1.08 g, 19 mmol), ammonium chloride (389 mg, 7.3 mmol) and ethanol/ water (50 mL, 4:1) was stirred at 80° C. for 4 h. After cooled, the mixture was filtered, and the resulting filtrate was poured into water and extracted with ethyl acetate. The organic layer was washed with water, dried, and concentrated under vacuum. The resulting residue was purified by column chromatography to give the title compound (420 mg, 48%), 1H NMR (CDCl3): δ7.05 (1H, d, J=8.8 Hz), 6.81 (1H, d, J=8.8 Hz), 5.46 (2H, br), 3.94 (3H, s), 3.92 (3H, s).
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