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

HRID 706469Notes

Reaction equation

HRID 706469 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-c3b87f20b3f8474c945fd1be4584da50
Source dataset
uspto-grants-2015_11
Patent number
US09174986B2

Reaction notes

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