Ethanol → HCID 178422929, compound

To 570 mg. (14.2 mmoles) of potassium metal dissolved in 10 ml. of absolute ethanol was added a mixture of 4.33 g. (14.2 mmoles) of 2-methyl-4-acetylpyridine oxime tosylate in 20 ml. of absolute ethanol and the resulting mixture stirred at room temperature for 1.5 hours. The reaction was quenched with 100 ml. of ether and the potassium tosylate removed by filtration. Gaseous hydrogen chloride was bubbled into the filtrate for 5 minutes and the solution was concentrated. The residue was dissolved in 50 ml. of water and the solution was made basic with solid potassium carbonate. The aqueous was extracted with (5×20 ml.) chloroform and the combined organic extracts dried and concentrated to dryness giving an oil. The residual oil was dissolved in 25 ml. of methanol, 1.75 g. (14.2 mmoles) of ethyl acetimidate hydrochloride was added and the mixture was heated to reflux for 1.5 hours. The mixture was concentrated and the residue taken up in 25 ml. of concentrated hydrochloric acid. The acid solution was heated on a steam bath for one hour, then allowed to stir at room temperature for 18 hours. The mixture was made basic with solid potassium carbonate and was extracted with (2×50 ml.) chloroform and (1×50 ml.) ethyl acetate. The combined extracts were dried and evaporated leaving an oil which solidified on trituration with a toluene/cyclohexane/acetone mixture, 530 mg. (22%), m.p. 115°-117° C.

1. additiona mixture of 4.33 g
2. customThe reaction was quenched with 100 ml
3. customof ether and the potassium tosylate removed by filtration
4. customGaseous hydrogen chloride was bubbled into the filtrate for 5 minutes
5. concentrationthe solution was concentrated
6. dissolutionThe residue was dissolved in 50 ml
7. extractionThe aqueous was extracted with (5×20 ml.) chloroform
8. customthe combined organic extracts dried
9. concentrationconcentrated to dryness
10. customgiving an oil
11. dissolutionThe residual oil was dissolved in 25 ml
12. temperaturethe mixture was heated
13. temperatureto reflux for 1.5 hours
14. concentrationThe mixture was concentrated
15. temperatureThe acid solution was heated on a steam bath for one hour
16. extractionwas extracted with (2×50 ml.) chloroform and (1×50 ml.) ethyl acetate
17. customThe combined extracts were dried
18. customevaporated
19. customleaving an oil which

ORD record

ord-d8ee4432fcba48ecbd96d28e5d01170c

Source dataset

uspto-grants-1981_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04302464