Hydrochloric Acid → HCID 9815456, Verbindung

Methyl 3-(2-nitroethyl)-1H-indole-4-carboxylate, Intermediate 9 (7.38 g, 29.8 mmol) was dissolved in methanol (200 mL) by heating and aqueous 2M HCl (460 mL) was added. Zinc powder (46.2 g, 706 mmol) was added portion vise by vigorous stirring. The resulting mixture was heated under reflux for 2 h. The hot reaction mixture was filtered and the filtrate was treated with aqueous 2M NaOH (560 mL) and filtered again. The filter cake was washed with methanol. The methanol was removed under reduced pressure and the aqueous mixture was extracted three times with ethyl acetate. The organic solution was washed with water and brine dried with magnesium sulfate, filtered and evaporated to dryness. It was obtained a yellowish crystalline material with the yield of 4.62 g. Recrystallisation from the dichlomethane-methanol mixture gave the product of very high purity. Mp. 234° C. MS m/z 187 [M+H]+.

1. temperatureby heating
2. temperatureThe resulting mixture was heated
3. temperatureunder reflux for 2 h
4. filtrationThe hot reaction mixture was filtered
5. additionthe filtrate was treated with aqueous 2M NaOH (560 mL)
6. filtrationfiltered again
7. washThe filter cake was washed with methanol
8. customThe methanol was removed under reduced pressure
9. extractionthe aqueous mixture was extracted three times with ethyl acetate
10. washThe organic solution was washed with water and brine
11. dry with materialdried with magnesium sulfate
12. filtrationfiltered
13. customevaporated to dryness
14. customIt was obtained a yellowish crystalline material with the yield of 4.62 g
15. customRecrystallisation from the dichlomethane-methanol mixture
16. customgave the product of very high purity

ORD-Eintrag

ord-a4f9c55ab03846fb87f2ecb69505f810

Quelldatensatz

uspto-grants-2012_03

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US08138333B2