Water → HCID 136386495, compound

Participants

Reaction Steps

To a mixture of phenyl(1H-pyrrolo[2,3-c]pyridin-2-yl)methanone (Example 35) (161 mg, 0.72 mmol) and hydroxylamine hydrochloride (100 mg, 1.45 mmol) in ethanol (3.6 mL) were added LiOH.H2O (120 mg, 2.16 mmol) and water (1.0 mL). The reaction mixture was heated under reflux until TLC analysis indicated consumption of the ketone. The mixture was concentrated to dryness. The residue was treated with water, and the residual solid was collected by filtration to give predominately one isomer of phenyl(1H-pyrrolo[2,3-c]pyridin-2-yl)methanone oxime (75.8 mg, 0.31 mmol, 44%) as a yellow solid. The aqueous filtrate was extracted with methylene chloride (3×). The combined extracts were washed with saturated NaCl, dried over Na2SO4, filtered, and concentrated to give ca. 1:1 mixture of isomers of the oxime (72 mg, 0.30 mmol, 42%) as a yellow solid:

Provenance & Evidence