Pyridine → 1-(5,6-Diphenyl-pyridin-2-yl)-ethanone Oxime

HRID 12558

Reaction equation

[C:1]1([C:7]2[CH:8]=[CH:9][C:10]([C:19](=O)[CH3:20])=[N:11][C:12]=2[C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[NH2:22][OH:23].Cl.N1C=CC=CC=1>CCO>[C:1]1([C:7]2[CH:8]=[CH:9][C:10]([C:19](=[N:22][OH:23])[CH3:20])=[N:11][C:12]=2[C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

Conditions

Temperature: 70 °C

Procedure

General Procedure P. 1-(5,6-Diphenyl-pyridin-2-yl)-ethanone (Compound 75, 119 mg, 0.44 mmol), NH2OH—HCl (103 mg, 1.48 mmol) and pyridine (272 mg, 0.27 mmol) was dissolved in EtOH (2 ml), and the mixture was heated to 70° C. under nitrogen for 3 hours. The reaction was quenched with water, and the product was extracted with ethyl acetate. The combined organic layers were washed with brine, and dried over Na2SO4. The filtered solvents were concentrated in vacuo, and the residue was purified by silica gel chromatography (15% ethyl acetate in hexane) to give title compound as an oil.

Workup

customThe reaction was quenched with water
extractionthe product was extracted with ethyl acetate
washThe combined organic layers were washed with brine
dry with materialdried over Na2SO4
concentrationThe filtered solvents were concentrated in vacuo
customthe residue was purified by silica gel chromatography (15% ethyl acetate in hexane)

Sources & evidence

ORD record: ord-30773829ed824d39bbfeeac19693c48b
Source dataset: uspto-grants-2010_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07728014B2

Linked notes

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