[OH-].[K+].[NH2:3][C:4]1[C:9]([Cl:10])=[CH:8][N:7]=[C:6](Cl)[C:5]=1[Cl:12].[CH3:13][O:14][CH2:15][CH2:16][OH:17]>>[NH2:3][C:4]1[C:9]([Cl:10])=[CH:8][N:7]=[C:6]([O:17][CH2:16][CH2:15][O:14][CH3:13])[C:5]=1[Cl:12]A solution of 16.5 grams (0.25 mole) of 86 percent potassium hydroxide dissolved in 100 milliliters of 2-methoxyethanol was added to a mixture of 49.5 grams (0.25 mole) of 4-amino-2,3,5-trichloropyridine in 150 milliliters of 2-methoxyethanol. The mixture was heated, with agitation, to 118° C. and held between 118°-120° C. for 31/2 hours. The reaction mixture was cooled to 75° C. and filtered under reduced pressure to remove the insoluble solids. The excess 2-methoxyethanol was evaporated off under reduced pressure and the liquid residue remaining was crystallized from hexane. The 4-amino-3,5-dichloro-2-(2-methoxyethoxy)pyridine product was recovered by filtration under reduced pressure, and obtained in a yield of 57 grams melting at 92°-93.5° C.
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