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ChemicalBook CAS DataBase List 5-METHOXY-PYRIDIN-2-YLAMINE
10167-97-2

5-METHOXY-PYRIDIN-2-YLAMINE synthesis

11synthesis methods
-

Yield:10167-97-2 100%

Reaction Conditions:

with hydroxylamine hydrochloride;triethylamine in ethanol;water; for 20 h;Heating / reflux;

Steps:

20.C

A mixture of 118 (1.0 equiv., 257 mmol, 52.0 g), hydroxylamine hydrochloride(6.5 equiv., 1671 mmol, 69.5 g), triethylamine (2.0 equiv., 514 mmol, 52.0 g), ethanol(400 ml) and water (200 ml) was refiuxed for 20 h. The solution was cooled and quenched with 2 M HCl, washed with isopropyl ether and the pH was adjusted to 9-10 with 6 M NaOH. The resulting mixture was extracted several times with dichloro- methane. The combined organic phases were dried with MgSO4 and the solvent was removed in vacuo. The oily residue was purified by column chromatography on silica gel (gradient elution: dichloromethane / ethyl acetate 25:75 -> ethyl acetate) to give 2-amino-5-methoxy-pyridine (119) (32.0 g, yield = 100 %). 1U NMR (δ, CDCl3): 3.74 (3H, s), 4.45 (2H, s {br) 6.45 (IH, d, J = 8.8 Hz), 7.07 (IH, dd, J = 8.8, 3.3 Hz), 7.72 (IH, d, J = 3.3 Hz)

References:

WO2007/113290,2007,A1 Location in patent:Page/Page column 40-42

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