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With hydrogenchloride; iron; In ethanol; at 60 - 65℃; for 0.5h;
In a flask, 107 mL of 80% ethanol and 30 g of the product of Step 2, The temperature was raised to 60 C, HCl was added, and Fe powder was added in batches. The temperature was controlled at 60-65 C. After the addition, the reaction was carried out for about 30 min, and the reaction was monitored by TLC under the following conditions: EpsilonAlpha:CH2Cl2 = 1:5. After the reaction, the solution was cooled to room temperature, adjusted to pH 8 with NaOH solution, and then filtered and dried. With 4 times the volume of dichloromethane temperature reflux dissolved to clarify, down to room temperature, adding petroleum ether in 17 g white product, the yield was 77.63%.
With iron; acetic acid; at 100℃; for 0.333333h;
Iron (1.0 g) was added to a solution of 2-chloro-5-methyl-4-nitropyridine N-oxide (500 mg, 2.6 mmol) in glacial acetic acid (10 mL). The reaction mixture was then heated at 100 C for 20 minutes. The suspension was poured onto aqueous NaOH (1M) and extracted with ethyl acetate. After drying over Na2S04, the solvent was then evaporated and the title compound was isolated as a colorless solid (370 mg, 2.6 mmol, HPLC Rt 1.3 min, FIA ES+ 143.0).
With iron; acetic acid; at 100℃; for 0.333333h;
4-Amino-2-chloro-5-methylpyridine (11) : Iron (1. 0 g) was added to a solution of 10 (500 mg, 2.6 mmol) in glacial acetic acid (10 mL). The reaction mixture was then heated at 100 C for 20 minutes. The suspension was poured on aqueous NaOH 1M and extracted with ethyl acetate. After drying over Na2SO4, the solvent was then evaporated and 11 was isolated as a colorless solid (370 mg, 2.6 mmol, HPLC Rt 1.3 min, FIA ES+ 143.0).
With iron; acetic acid; In tetrahydrofuran; methanol; at 30 - 80℃; for 0.666667h;
To a mixture of 2-chloro-5-methyl-4-nitropyridine 1 -oxide (50 g, 265 mmol) in acetic acid (200 mL) was added iron (74.0 g, 1326 mmol) at 30 C. The solution was stirred at 80 C for 40 min. The mixture was poured into aq. NaOH (1M, 4000 mL) and extracted with EtOAc (1000 mL x 3). The combined organic layers were washed with brine (800 mL), dried over anhydrous Na2S04 and filtered. The filtrate was concentrated in vacuum to give 2-chloro-5- methylpyridin-4-amine as a light yellow oil, which was used directly without further purification. MS: 143 (M + 1). 1H MR (400 MHz, d4-methanol) delta 7.65 (s, 1H), 6.55 (s, 1H), 2.03 (s, 3H).
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