Hydroxyamine hydrochloride → 6-Chloro-2-methylnicotinaldehyde oxime

HRID 386023Notes

Reaction equation

HRID 386023 reaction equation
[Cl:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=O)=[C:4]([CH3:10])[N:3]=1.Cl.[NH2:12][OH:13].C([O-])(=O)C.[Na+]>C(O)C>[Cl:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[N:12][OH:13])=[C:4]([CH3:10])[N:3]=1

Participants

5

Reactant 3

HCID 443297Hydroxyamine hydrochlorideHCID 517045Sodium AcetateHCID 447548676-Chloro-2-methylpyridine-3-carbaldehyde

Product 1

HCID 723159756-Chloro-2-methylnicotinaldehyde oxime

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

6-Chloro-2-methylnicotinaldehyde (1 g, 6.43 mmol), hydroxylamine hydrochloride (0.45 g, 6.43 mmol), and sodium acetate (0.53 g, 6.43 mmol) were dissolved in dry ethanol (32 ml) and transferred to a flame-dried round bottom flask. The reaction was allowed to stir at room temperature for 20 minutes. It was then concentrated under reduced pressure, re-dissolved in ethyl acetate, and washed with water. The aqueous layer was extracted with ethyl acetate two times. The organic layers were combined, dried over magnesium sulfate, filtered, and concentrated under reduced pressure. Purification was performed via silica gel chromatography (0-100% ethyl acetate in hexane) to afford the title compound.

Workup

  1. customtransferred to a flame-dried round bottom flask
  2. concentrationIt was then concentrated under reduced pressure
  3. dissolutionre-dissolved in ethyl acetate
  4. washwashed with water
  5. extractionThe aqueous layer was extracted with ethyl acetate two times
  6. dry with materialdried over magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure
  9. customPurification

Sources & evidence

ORD record
ord-0c556354f091421a9426b2081ce36d16
Source dataset
uspto-grants-2013_02
Patent number
US08367706B2

Reaction notes

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