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ChemicalBook CAS DataBase List 3-AMINO-6-CHLORO-5-METHOXY PYRIDINE
75711-01-2

3-AMINO-6-CHLORO-5-METHOXY PYRIDINE synthesis

3synthesis methods
-

Yield: 93%

Reaction Conditions:

Stage #1:2-chloro-3-methoxy-5-nitropyridine with water;tin(ll) chloride in ethyl acetate at 20; for 1 h;
Stage #2: with sodium hydroxide in water;ethyl acetate

Steps:

46
To a stirred solution of 2-chloro-3-(methyloxy)-5-nitropyridine (3.00 g, 15.90 mmol) in EtOAc (75 ml) was added SnCl2 dihydrate (21.54 g, 95.00 mmol) and the resulting mixture was stirred at room temperature for 1 h. The reaction mixture was quenched with aqueous NaOH and extracted with EtOAc (5×75 ml). The collected organic layers were washed with water (3×75 ml), dried (Na2SO4), filtered and evaporated under reduced pressure to give the title compound D46 (2.34 g, 14.80 mmol, 93% yield) as a brown solid.UPLC: rt=0.43 min, peaks observed: 159 (M+1, 100%) and 161 (M+1, 33%). C6H7ClN2O requires 158.1H NMR (400 MHz, DMSO-d6) δ (ppm): 7.29 (d, 1H), 6.71 (d, 1H), 5.50 (bs, 2H), 3.77 (s, 3H).

References:

ALVARO, GIUSEPPE;AMANTINI, DAVID;BELVEDERE, SANDRO US2009/22670, 2009, A1 Location in patent:Page/Page column 22

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