Methyl Acrylate → methyl (E)-3-(3-quinolinyl)-2-propenoate

In an amount of 10.2 g of 3-bromoquinoline was stirred together with 7 ml of methyl acrylate, 110 mg of palladium(II) acetate, 599 mg of tri-o-tolylphosphine, and 29 ml of triethylamine at 100° C. for 17 hours in a sealed tube. The reaction mixture was diluted with 300 ml of chloroform, and successively washed with 250 ml of saturated brine, and 250 ml of saturated aqueous ammonium chloride. The organic layer was dried over anhydrous sodium sulfate, and then filtered, and the filtrate was concentrated under reduced pressure. The resulting residue was dissolved in 80 ml of chloroform, added with 200 ml of hexane under ice cooling, and stirred for 30 minutes. The precipitates were taken by filtration, washed with hexane, and then dried under reduced pressure to obtain 8.0 g of methyl (E)-3-(quinolin-3-yl)acrylate. Physicochemical Properties of this Compound

1. washsuccessively washed with 250 ml of saturated brine, and 250 ml of saturated aqueous ammonium chloride
2. dry with materialThe organic layer was dried over anhydrous sodium sulfate
3. filtrationfiltered
4. concentrationthe filtrate was concentrated under reduced pressure
5. dissolutionThe resulting residue was dissolved in 80 ml of chloroform
6. additionadded with 200 ml of hexane under ice cooling
7. filtrationThe precipitates were taken by filtration
8. washwashed with hexane
9. customdried under reduced pressure

ORD-Eintrag

ord-a5cbe1bea1f141bd98df28de0a72be4a

Quelldatensatz

uspto-grants-2008_04

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US07365174B2