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

HRID 706470Notes

Reaction equation

HRID 706470 reaction equation
[CH2:1]([O:3][C:4]1[CH:5]=[C:6]([CH:10]=[CH:11][C:12]=1[O:13][CH2:14][C:15]1[CH:16]=[N:17][C:18]([O:21][CH3:22])=[CH:19][CH:20]=1)[CH:7]=[N:8]O)[CH3:2]>C(O)(=O)C.C(OCC)(=O)C.[Zn]>[CH2:1]([O:3][C:4]1[CH:5]=[C:6]([CH2:7][NH2:8])[CH:10]=[CH:11][C:12]=1[O:13][CH2:14][C:15]1[CH:16]=[N:17][C:18]([O:21][CH3:22])=[CH:19][CH:20]=1)[CH3:2]

Participants

5

Reactant 1

HCID 1317330123-Ethoxy-4-((6-methoxypyridin-3-yl)methoxy)benzaldehyde oxime

Product 1

HCID 118114093(3-Ethoxy-4-((6-methoxypyridin-3-yl)methoxy)phenyl)methanamineYield 95%

Reagents, catalysts & solvents 3

HCID 23994ZincCatalystHCID 176Acetic AcidSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
65 °C

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-1bc3a010a17e4dc7bfbd6de057497ea3
Source dataset
uspto-grants-2015_11
Patent number
US09174986B2

Reaction notes

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