3-Ethoxy-4-((6-methoxypyridin-3-yl)methoxy)benzaldehyde oxime → (3-Ethoxy-4-((6-methoxypyridin-3-yl)methoxy)phenyl)methanamine

Temperature

65 °C

To a stirred solution of 3-ethoxy-4-((6-methoxypyridin-3-yl)methoxy)benzaldehyde oxime (3.05 g, 10.09 mmol) in acetic acid (25 mL) was added zinc (3.30 g, 50.44 mmol). The resulting mixture was heated to 65° C. After 2 h, the gray suspension was allowed to cool to room temperature and was diluted with ethyl acetate (150 mL). The mixture was filtered through Celite with the aid of additional ethyl acetate (50 mL). The filtrate was diluted with water (50 mL) and made basic by the addition of concentrated ammonium hydroxide solution (˜30 mL). The phases were separated, and the aqueous phase was extracted with ethyl acetate (50 mL). The combined organic phases were dried over magnesium sulfate, filtered, and concentrated to provide 2.75 g (95%) of (3-ethoxy-4-((6-methoxypyridin-3-yl)methoxy)phenyl)methanamine as a yellow oil.

1. temperatureto cool to room temperature
2. filtrationThe mixture was filtered through Celite with the aid of additional ethyl acetate (50 mL)
3. additionThe filtrate was diluted with water (50 mL)
4. additionmade basic by the addition of concentrated ammonium hydroxide solution (˜30 mL)
5. customThe phases were separated
6. extractionthe aqueous phase was extracted with ethyl acetate (50 mL)
7. dry with materialThe combined organic phases were dried over magnesium sulfate
8. filtrationfiltered
9. concentrationconcentrated

ORD record

ord-5f46d4fdccfb4b6186cdeda616e6c3f0

Source dataset

uspto-grants-2015_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09067914B1