반응 #1341001

반응 방정식

2-Fluoro-4-bromoaniline

crotonaldehyde

ammonia

→

title compound

수율 47.0%

6-bromo-8-fluoro-2-methylquinoline

수율 47.0%

용매

HCl

반응 조건

후처리

1. 1
   온도The mixture was heated
2. 2
   온도to reflux
3. 3
   온도The resulting mixture was heated for an additional 90 minutes
4. 4
   추출The mixture was extracted with ethyl acetate
5. 5
   세척the organic layer was washed with water and brine
6. 6
   건조dried over magnesium sulfate
7. 7
   여과filtered
8. 8
   농축concentrated in vacuo
9. 9
   기타The residue was purified by flash column chromatography
10. 10
    세척eluting with 15-10% ethyl acetate/petrol
11. 11
    workup.ADDITIONThe product containing fractions
12. 12
    농축concentrated to ca 60 ml
13. 13
    기타The product was then isolated by filtration
14. 14
    세척The filter cake was washed with petrol and air
15. 15
    기타dried

실험 절차

2-Fluoro-4-bromoaniline (10 g, 0.053 mol) was slurried in 6M HCl (100 ml). The mixture was heated to reflux and crotonaldehyde (14.9 g, 0.212 mol) was added dropwise over 1 hour. The resulting mixture was heated for an additional 90 minutes, then cooled down to room temperature and neutralized by careful addition of concentrated ammonia solution. The mixture was extracted with ethyl acetate and the organic layer was washed with water and brine, dried over magnesium sulfate, filtered and concentrated in vacuo. The residue was purified by flash column chromatography, eluting with 15-10% ethyl acetate/petrol. The product containing fractions were combined and concentrated to ca 60 ml. The product was then isolated by filtration. The filter cake was washed with petrol and air dried to afford the title compound as a solid (5.96 g, 47% yield). 1H NMR (CDCl3, 400 MHz) 2.80 (3H, s), 7.38 (1H, d), 7.53 (1H, d), 7.76 (1H, s), 8.00 (1H, d); MS (ES+) 240/242.

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