Hydroxyamine hydrochloride → HCID 136388331, compound

HRID 1060862Notes

Reaction equation

HRID 1060862 reaction equation
[CH3:1][C:2]1[C:3]([O:13][C:14]2[C:19]([CH3:20])=[CH:18][C:17]([CH3:21])=[CH:16][C:15]=2[CH3:22])=[N:4][C:5]([CH3:12])=[CH:6][C:7]=1[C:8](=O)[CH2:9][CH3:10].Cl.[NH2:24][OH:25].C([O-])(=O)C.[Na+]>C(O)C>[CH3:1][C:2]1[C:3]([O:13][C:14]2[C:19]([CH3:20])=[CH:18][C:17]([CH3:21])=[CH:16][C:15]=2[CH3:22])=[N:4][C:5]([CH3:12])=[CH:6][C:7]=1[C:8](=[N:24][OH:25])[CH2:9][CH3:10]

Participants

5

Reactant 3

HCID 443297Hydroxyamine hydrochlorideHCID 517045Sodium AcetateHCID 12970226HCID 12970226, compound

Product 1

HCID 136388331HCID 136388331, compoundYield 88.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 1-[3,6-dimethyl-2-(2,4,6-trimethyl-phenoxy)-pyridin-4-yl]-propan-1-one (330 mg, 1.11 mmol), hydroxylamine hydrochloride (230.4 mg, 3.33 mmol), and sodium acetate (273 mg, 3.33 mmol) in ethanol (25 ml) was stirred at room temperature over a weekend. The mixture was concentrated to dryness, then diluted with water, and extracted with chloroform. The organic layer was separated, dried over sodium sulfate and concentrated to dryness to give 306 mg of a mixture of the title (E) and (Z)-isomers as a white solid.

Workup

  1. concentrationThe mixture was concentrated to dryness
  2. additiondiluted with water
  3. extractionextracted with chloroform
  4. customThe organic layer was separated
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-f9fd2af87977448eadeebb6f6bf056ed
Source dataset
uspto-grants-2003_02
Patent number
US06525067B1

Reaction notes

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