2-phenyl-1-(pyridin-2-yl)ethanone → HCID 136230336, compound

This compound was prepared by suitable modification of the procedures described by Niemers and Hiltman, Synthesis, 1976, 593 as follows. To a solution of 1-(2-pyridinyl)-2-phenylethanone (Case and Buttle, J. Org. Chem., 1961, 26, 4415) (49.05 g, 0.249 mol) in 95% ethanol (400 ml) was added a solution of hydroxylamine hydrochloride (51.91 g, 0.747 mol) in 10% sodium hydroxide (200 ml). The solution was heated to reflux under nitrogen for 1.25 hours, and stirred at room temperature for 48 hours. The majority of the solvent was removed and the residue was added to water (500 ml). The aqueous solution was extracted with ether (1×1000 ml, and 3×250 ml). The combined ether extracts were washed with saturated NaCl and dried over MgSO4. Removal of solvent gave 55.61 g of the crude product as a brown solid. The above solid was dissolved in cyclohexane (400 ml) and ether (500 ml) and filtered while hot. The filtrate was concentrated to a volume of 500 ml and cooled to room temperature. The solid which formed was isolated by filtration to yield 20.77 g of 1-(2-pyridinyl)-2-phenylethanone oxime; mp 151°-153° C.

1. customThis compound was prepared by suitable modification of the procedures
2. customdescribed by Niemers and Hiltman, Synthesis, 1976, 593
3. temperatureThe solution was heated
4. temperatureto reflux under nitrogen for 1.25 hours
5. customThe majority of the solvent was removed
6. additionthe residue was added to water (500 ml)
7. extractionThe aqueous solution was extracted with ether (1×1000 ml, and 3×250 ml)
8. washThe combined ether extracts were washed with saturated NaCl
9. dry with materialdried over MgSO4
10. customRemoval of solvent
11. customgave 55.61 g of the crude product as a brown solid
12. filtrationether (500 ml) and filtered while hot
13. concentrationThe filtrate was concentrated to a volume of 500 ml
14. temperaturecooled to room temperature
15. customThe solid which formed
16. customwas isolated by filtration

ORD record

ord-035c159719d4400ea688f60502e0b4fb

Source dataset

uspto-grants-1988_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04769466