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

HRID 2178350Notes

Reaction equation

HRID 2178350 reaction equation
[CH2:1]([O:3][C:4]1[CH:5]=[C:6]([CH:9]=[CH:10][C:11]=1[O:12][CH2:13][C:14]1[CH:15]=[N:16][C:17]([O:20][CH3:21])=[CH:18][CH:19]=1)[CH:7]=O)[CH3:2].[OH2:22].Cl.[NH2:24]O>CO.N1C=CC=CC=1>[CH2:1]([O:3][C:4]1[CH:5]=[C:6]([CH:9]=[CH:10][C:11]=1[O:12][CH2:13][C:14]1[CH:15]=[N:16][C:17]([O:20][CH3:21])=[CH:18][CH:19]=1)[CH:7]=[N:24][OH:22])[CH3:2]

Participants

6

Reactant 3

HCID 962WaterHCID 443297Hydroxyamine hydrochlorideHCID 1181140283-Ethoxy-4-((6-methoxypyridin-3-yl)methoxy)benzaldehyde

Product 1

HCID 1317330123-Ethoxy-4-((6-methoxypyridin-3-yl)methoxy)benzaldehyde oximeYield 85%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 1049PyridineSolvent

Procedure

To a stirred solution of 3-ethoxy-4-((6-methoxypyridin-3-yl)methoxy)benzaldehyde (3.40 g, 11.83 mmol) in methanol (50 mL), pyridine (1.5 mL), and water (5 mL) was added hydroxylamine hydrochloride (1.23 g, 17.75 mmol). The reaction mixture was heated to reflux. After 2 h, the colorless solution was allowed to cool to room temperature and was concentrated. The residue was suspended in water (50 mL) and filtered. The solids were washed with water and then dissolved in ethyl acetate (150 mL). The solution was dried over magnesium sulfate, filtered, and concentrated to provide 3.05 g (85%) of 3-ethoxy-4-((6-methoxypyridin-3-yl)methoxy)benzaldehyde oxime as an off-white solid.

Workup

  1. temperatureThe reaction mixture was heated to reflux
  2. concentrationwas concentrated
  3. filtrationfiltered
  4. washThe solids were washed with water
  5. dissolutiondissolved in ethyl acetate (150 mL)
  6. dry with materialThe solution was dried over magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-5b7f5f1d33b845548967a7ad0c8dc650
Source dataset
uspto-grants-2015_06
Patent number
US09067914B1

Reaction notes

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