1-(3-Methoxy-4-((6-methoxypyridin-3-yl)methoxy)phenyl)ethan-1-one oxime → 1-(3-Methoxy-4-((6-methoxypyridin-3-yl)methoxy)phenyl)ethan-1-amine

HRID 2178390Notes

Reaction equation

[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:19](=[N:21]O)[CH3:20])[CH:6]=[CH:7][C:8]=1[O:9][CH2:10][C:11]1[CH:12]=[N:13][C:14]([O:17][CH3:18])=[CH:15][CH:16]=1>C(O)(=O)C.[Zn]>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:19]([NH2:21])[CH3:20])[CH:6]=[CH:7][C:8]=1[O:9][CH2:10][C:11]1[CH:12]=[N:13][C:14]([O:17][CH3:18])=[CH:15][CH:16]=1

Participants

Conditions

Temperature: 65 °C

Procedure

To a stirred solution of 1-(3-methoxy-4-((6-methoxypyridin-3-yl)methoxy)phenyl)ethan-1-one oxime (5.55 g, 18.36 mmol) in acetic acid (40 mL) was added zinc dust (6.00 g, 91.79 mmol). The resulting mixture was heated to 65° C. After 1 h, the mixture was allowed to cool to room temperature and was filtered through Celite. The filtercake was washed with methanol (100 mL). The filtrate was concentrated, and the residue dissolved in 5N ammonium hydroxide solution (75 mL). The mixture was extracted with chloroform (2×50 mL). The combined organic phases were dried over magnesium sulfate, filtered, and concentrated to provide 4.56 g (86%) of 1-(3-methoxy-4-((6-methoxypyridin-3-yl)methoxy)phenyl)ethan-1-amine as a yellow oil.

Workup

temperatureto cool to room temperature
filtrationwas filtered through Celite
washThe filtercake was washed with methanol (100 mL)
concentrationThe filtrate was concentrated
dissolutionthe residue dissolved in 5N ammonium hydroxide solution (75 mL)
extractionThe mixture was extracted with chloroform (2×50 mL)
dry with materialThe combined organic phases were dried over magnesium sulfate
filtrationfiltered
concentrationconcentrated

Sources & evidence

ORD record: ord-70d1781c925f43d1abb51cac4e4eab70
Source dataset: uspto-grants-2015_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09067914B1

Reaction notes

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