反应详情

Into a 500 mL PARR reactor bottle was placed 6.3 gram (30 mmol) of 6-diethylamino-3-nitro-2-picoline and 75 mL of reagent grade methanol. The mixture was stirred at room temperature for a few minutes to fully dissolve the diethylaminonitropicoline, then 1 gram of 5% Palladium on carbon was added. The resulting mixture was placed upon the PARR hydrogenation shaker and hydrogenated at 50 psi H2 atmosphere at room temperature. After 3 hours the reaction was removed from the hydrogenation shaker and evaluated by thin layer chromatography to show that all starting material had been consumed and one product had formed. The product containing methanol solution was filtered through a pad of Supercel Celite slurried in methanol on a medium porosity sintered glass funnel to remove the palladium on carbon catalyst. The Celite pad was washed with 25 mL of methanol. The resulting nearly colorless filtrate was treated with 7 mL of concentrated hydrochloric acid (0.84 moles hydrogen chloride) and the lightly colored solution was transferred to a 500 mL flask. The product mixture was concentrated under reduced pressure at 50° C. to afford a wet amorphous semi-solid product mixture. This was treated with 50 mL of acetonitrile and stirred rapidly for 45 minutes then filtered on a Buchner funnel. The resulting off-white solid was washed with 25 mL of acetonitrile, dried by sucking air through for 30 minutes, then dried under high vacuum over night. The off-white product of N2,N2-diethyl-6-methyl-2,5-pyridinediamine dihydrochloride was 7.2 grams (28.5 mmol, 95.1% yield). Mass Spectrum analysis indicated an Electron Impact EI+ m/e of 179.

1. customwas placed upon the PARR hydrogenation shaker and hydrogenated at 50 psi H2 atmosphere at room temperature
2. customAfter 3 hours the reaction was removed from the hydrogenation shaker
3. customhad been consumed
4. customone product had formed
5. filtrationwas filtered through a pad of Supercel Celite
6. customslurried in methanol on a medium porosity sintered glass funnel
7. customto remove the palladium on carbon catalyst
8. washThe Celite pad was washed with 25 mL of methanol
9. customthe lightly colored solution was transferred to a 500 mL flask
10. concentrationThe product mixture was concentrated under reduced pressure at 50° C.
11. customto afford a wet amorphous semi-solid product mixture
12. stirringstirred rapidly for 45 minutes
13. filtrationthen filtered on a Buchner funnel
14. washThe resulting off-white solid was washed with 25 mL of acetonitrile
15. customdried
16. customthrough for 30 minutes
17. customdried under high vacuum over night