2-Amino-3-methoxypyridine

solid

To a solution of 2-nitro-3-methoxypyridine (32 g, 208 mmol) in EtOAc (150 mL) and MeOH (35 mL) under a nitrogen atmosphere was added 10percent palladium on carbon (1.5 g, 1.4 mmol). To a solution of 2-nitro-3- methoxypyridine (32 g, 208 mmol) in EtOAc (150 mL) and MeOH (35 mL) under a nitrogen Preparation of 3-methoxypyhdin-2-amine (the compound of formula (II))A suspension of 3-methoxy-2-nitropyridin (30 g, 194.8 mmol) and 10percent Pd/C ( 10 g) in ethanol ( 1 L) was hyd rogenated in a par hyd rogenator (H[00108] As shown in step 6-i of Scheme 6, calcium chloride (4.0 g, 35.7 mmol) was added to a stirring solution of 3-methoxy-2-nitropyridine (5.0 g, 32.5 mmol, obtained from AK Scientific, Inc.) in methanol (100 mL) and water (25 mL). The reaction mixture was warmed to 75 As shown in step 6-i of Scheme 6, calcium chloride (4.0 g, 35.7 mmol) was added to a stirring solution of 3-methoxy-2-nitropyridine (5.0 g, 32.5 mmol, obtained from AK Scientific, Inc.) in methanol (100 mL) and water (25 mL). The reaction mixture was warmed to 75 As shown in step 2-i of Scheme 2, to a stirred solution of 3-methoxy-2-nitropyridine (compound 1001, 50.0 g, 325.0 mmol) in ethanol (1.0 L) and HTo a stirred solution of 3-(methyloxy)-2-nitropyridine (1.00 g, 6.49 mmol) in EtOH (13 ml), a 2 M HCl aqueous solution (1.34 ml, 2.68 mmol) and iron (2.44 g, 43.70 mmol) were added at 0° C. The resulting mixture was stirred for 2.5 h at room temperature. Celite (2.40 g) was added. The mixture was then filtered through a celite pad and evaporated to give a dark oil that was eluted through a SCX column. Collected fractions gave the title compound D34 (0.50 g, 3.62 mmol, 56percent yield) as a dark green solid. 3-Methoxy-2-nitro-pyridine (53, 7.00 g, 45.4 mmol) in 100 mL of methanol, was degassed and palladium (0.7 g, 20percent) was added. The reaction was stirred at room temperature for one day under a hydrogen balloon. The reaction was filtered through celite and the filtrate concentrated under vacuum to provide the desired compound (54, 5.555 g). MS (ESI) [M+H