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A suspension of sodium methoxide (40.5 g, 0.750 mol) in 200 mL of methanol was slowly added to a solution of 2-chloro-3- nitro-pyridine (79.3 g, 0.500 mol) in 800 mL of methanol at 0 °C. The reaction mixture was stirred for 4 hours and then poured into 1000 g of ice. The resulting precipitate was filtered, washed with water, and dried to give 2-methoxy-3-nitro-pyridine (70. g, 0.45 mmol, 90 percent) as a white solid.
With hydrogen;palladium 10% on activated carbon; In methanol; for 4h;
(1)10percent palladium-activated carbon (2.5 g) was added to a solution of commercially available <strong>[20265-35-4]2-methoxy-3-nitropyridine</strong> (50.5 g) in methanol (500 mL), and the mixture was stirred for four hours in a hydrogen atmosphere.The reaction solution was filtered through celite, and then the filtrate was concentrated under reduced pressure.The resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate=8:1) to give 2-methoxypyridin-3-amine as a yellow powder (37.2 g, 92percent).1H NMR (300 MHz, CDCl3) delta ppm 3.64-3.88 (m, 2H), 3.92-4.05 (m, 3H), 6.67-6.76 (m, 1H), 6.84-6.92 (m, 1H), 7.54-7.62 (m, 1H).MS(+): 125 [M+H]+.
90%
palladium-carbon; In ethanol;
EXAMPLE 13 Synthesis of 2-methoxy-3-aminopyridine STR28 To a solution of the compound of Example 12 (17.12 g, 0.11 mol) in ethanol (180 mL) in a Parr bottle, was added 4percent Pd/C (3.43 g). The bottle was sealed, purged with nitrogen and was pressurized (5 psi) with hydrogen. After stirring at room temperature for 2 hr, the reaction vessel was vented, purged with nitrogen and filtered. The clear filtrate was concentrated to give the title compound (15.3 g, 90percent). 1 H NMR (CDCl3): 7.58 (dd, J=5, 2 Hz, 1H); 6.87 (dd, J=8, 2 Hz, 1H); 6.72 (dd, J=8, 5 Hz, 1H); 3.98 (s, 3H).
87%
With hydrogen;palladium 10% on activated carbon; In methanol; for 15h;
A solution of 2- methoxy-3-nitro-pyridine (70. g, 0.45 mol) in methanol (700 mL) containing palladium on carbon (7 g, 10 percent) was stirred under an atmosphere of hydrogen for 15 hours. The catalyst was filtered and washed with methanol. The filtrate was evaporated to dryness to give crude 2- methoxy-pyridin-3-ylamine (48 g, 0.39 mol, 87 percent), which was used directly in the next step.
74%
With hydrogen;palladium 10% on activated carbon; In methanol;
Compound 1 (20.8 g, 135 mmol) was dissolved in methanol (270 mL) and palladium on carbon (10percent Pd dry weight basis, Degussa type E101 NE/W, 50percent water content, 5.75 g, 2.7 mmol Pd) was added. The atmosphere was replaced with hydrogen (toggle between vacuum and hydrogen from a balloon five times), the mixture was stirred overnight, then filtered. The filtrate was concentrated under vacuum and the residue was taken up in a 1:1 hexanes:ethyl acetate mixture and washed with a 4:1 mixture of water and saturated NaHCO3, saturated NaHCO3 and brine. The organic layer was dried over MgSO4 and filtered and the filtrate was concentrated under reduced pressure to give compound 2 (12.43 g, 74percent) as a white solid. This material was used without purification.
38.9 g
With palladium 10% on activated carbon; hydrogen; In methanol; for 3h;
A solution of <strong>[20265-35-4]2-methoxy-3-nitropyridine</strong> (50 g, 324.4 mmol) and 10percent Pd/C (5 g) in MeOH (500 ml_) was stirred under an atmosphere of H2 for 3 h. The mixture was filtered through celite and the filter was washed with MeOH. The filtrate was concentrated in vacuo to yield 2-methoxypyridin-3-amine as a brown solid (38.9 g, 313.4 mmol). 1H NMR: (300 MHz, CDCI3) delta: 3.74 (br. s, 2H), 3.96 (s, 3H), 6.72 (m, 1 H), 6.86 (m, 1 H), 7.56 (d, J=1.8, 1 H)
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