Hydroxyamine hydrochloride → HCID 136408096, compound

HRID 1480634Notes

Reaction equation

HRID 1480634 reaction equation
Cl.[NH2:2][OH:3].[C:4]([C:8]1[CH:9]=[C:10]([C:17]2[CH:18]=[N:19][C:20]([C:23]([F:26])([F:25])[F:24])=[CH:21][CH:22]=2)[C:11]([OH:16])=[C:12]([CH:15]=1)[CH:13]=O)([CH3:7])([CH3:6])[CH3:5].C([O-])(=O)C.[Na+]>C(O)C>[C:4]([C:8]1[CH:9]=[C:10]([C:17]2[CH:18]=[N:19][C:20]([C:23]([F:26])([F:25])[F:24])=[CH:21][CH:22]=2)[C:11]([OH:16])=[C:12]([CH:15]=1)[CH:13]=[N:2][OH:3])([CH3:7])([CH3:6])[CH3:5]

Participants

5

Reactant 3

HCID 443297Hydroxyamine hydrochlorideHCID 517045Sodium AcetateHCID 86718581HCID 86718581, compound

Product 1

HCID 136408096HCID 136408096, compoundYield 83%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Following the patent procedure of C. G. Luca (US 20050137168), hydroxylamine hydrochloride (355 mg, 5.11 mmol) was added to a solution of 5-(tert-butyl)-2-hydroxy-3-(6-(trifluoromethyl)pyridin-3-yl)benzaldehyde (from Example 47, Step 1) (1.5 g, 4.64 mmol) and sodium acetate (419 mg, 5.11 mmol) in ethanol (15 mL). The reaction was stirred at room temperature for 16 hours. The mixture was partitioned between water and ethyl acetate and the organic phase separated, dried (Na2SO4), filtered and the solvent removed under reduced pressure. The residue was purified using flash chromatography on silica eluting with a solvent gradient of 0 to 100% ethyl acetate in hexanes to give 5-(tert-butyl)-2-hydroxy-3-(6-(trifluoromethyl)pyridin-3-yl)benzaldehyde oxime (1.3 g, 83% yield).

Workup

  1. customThe mixture was partitioned between water and ethyl acetate
  2. customthe organic phase separated
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. customthe solvent removed under reduced pressure
  6. customThe residue was purified

Sources & evidence

ORD record
ord-c5bf5e9b8a4a4a43986f9393ed58d416
Source dataset
uspto-grants-2016_08
Patent number
US09409893B2

Reaction notes

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