Hydroxyamine hydrochloride → HCID 136408096, compound

Participants

Reaction Steps

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).

Provenance & Evidence