반응 #582456

반응 방정식

2-methylquinolin-8-amine

6-methyl-2-bromopyridine

sodium tert-butoxide

→

tan solid

수율 68.0%

2-Methyl-N-(6-methylpyridin-2-yl)quinolin-8-amine

수율 68.0%

용매

toluene

반응 조건

후처리

1. 1
   기타The mixture was purged thoroughly with nitrogen and 44 mg of 1,1′-bis(diphenylphosphino)ferrocene and 18 mg of palladium acetate
2. 2
   workup.ADDITIONwere added
3. 3
   온도The reaction mixture was heated to 80 C for 16 hours
4. 4
   온도cooled to 22 C
5. 5
   기타After quenching with 100 ml of water
6. 6
   추출the product was extracted with 75 ml ethyl acetate
7. 7
   추출The product was extracted with 120 ml of 1M hydrochloric acid
8. 8
   추출extraction with 75 ml of ethyl acetate
9. 9
   세척washing with 30 ml of water
10. 10
    기타the solvent was removed
11. 11
    기타The product was purified
12. 12
    workup.DISSOLUTIONby dissolving in a hot mixture of 20 ml of 2-propanol and 5 ml of water
13. 13
    온도after cooling to 5 C
14. 14
    여과the product was filtered
15. 15
    세척washed with 50% 2-propanol
16. 16
    기타dried

실험 절차

To a flask were added 4.2 g of 2-methylquinolin-8-amine, 4.6 g of 6-methyl-2-bromopyridine, 3.3 g of sodium tert-butoxide, and 75 ml toluene. The mixture was purged thoroughly with nitrogen and 44 mg of 1,1′-bis(diphenylphosphino)ferrocene and 18 mg of palladium acetate were added. The reaction mixture was heated to 80 C for 16 hours, and then cooled to 22 C. After quenching with 100 ml of water, the product was extracted with 75 ml ethyl acetate. The product was extracted with 120 ml of 1M hydrochloric acid, and then basified with 3M sodium hydroxide. Following extraction with 75 ml of ethyl acetate and washing with 30 ml of water, the solvent was removed. The product was purified by dissolving in a hot mixture of 20 ml of 2-propanol and 5 ml of water, and after cooling to 5 C, the product was filtered, washed with 50% 2-propanol, and dried, resulting in 4.5 g of a tan solid.

출처