Water → 3-(2-Methyl-5-pyridinyl)-2-cyclohexen-1-one

A 72.2 g. portion of 1-(2-methyl-5-pyridinyl)hexan-1,5-dione was dissolved in 200 ml. of methanol and added to a solution containing 50 g. of sodium hydroxide in 500 ml. of water plus 100 ml. of methanol. The reaction mixture was stirred for one hour at room temperature and the methanol was then distilled off in vacuo at a low temperature. The remaining aqueous mixture was extracted four times with ether; the ether extracts were combined, dried over anhydrous sodium sulfate and filtered; and, the dried ether solution was stripped in vacuo to remove the ether and to yield 54 g. (82% yield) of 3-(2-methyl-5-pyridinyl)-2-cyclohexen-1-one. This 54 g. portion of 2-(2-methyl-5-pyridinyl)-2-cyclohexen-1-one was converted, as in Example C-3, to 36.0 g. (62% yield) of the corresponding oxime derivative, m.p. 171°-173° C. The 10 g. portion of this oxime was converted, as in Example D-3, to 6.4 g. of 5-(3-aminophenyl)-2-methylpyridine, m.p. 115°-116° C., using 8.5 ml. of acetic anhydride and 70 ml. of acetic acid and gaseous hydrogen chloride for one hour while heating the reaction mixture at 80°-90° C.

1. additioncontaining 50 g
2. distillationthe methanol was then distilled off in vacuo at a low temperature
3. extractionThe remaining aqueous mixture was extracted four times with ether
4. dry with materialdried over anhydrous sodium sulfate
5. filtrationfiltered
6. customto remove the ether
7. customto yield 54 g

ORD record

ord-bd8b95fff4374bb58cfd4d642b74eda0

Source dataset

uspto-grants-1978_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04111946