3-(1-methyl-1,2,3,6-tetrahydropyridin-4-yl)-5-nitro-1H-indole → 5-Nitroindole

To a solution of 38.2 gm (145 mMol) 5-nitro-3-(1-methyl-1,2,3,6-tetrahydropyridin-4-yl)-1H-indole in 1.9 L ethanol and 30 mL 5N HCl were added 10.0 gm 5% palladium on carbon. The reaction mixture was hydrogenated at ambient for 18 hours with an initial hydrogen pressure of 60 p.s.i. The reaction mixture was filtered and then concentrated under reduced pressure. The residue was dissolved in methanol and the solution filtered. This filtrate was concentrated under reduced pressure and the residue redissolved in ethanol. The solution was concentrated to about 500 mL and product allowed to crystallize. The crystals were filtered to give 48.9 gm (95%) of the title compound as its dihydrochloride salt, ethanol solvate.

1. customambient for 18 hours
2. filtrationThe reaction mixture was filtered
3. concentrationconcentrated under reduced pressure
4. dissolutionThe residue was dissolved in methanol
5. filtrationthe solution filtered
6. concentrationThis filtrate was concentrated under reduced pressure
7. dissolutionthe residue redissolved in ethanol
8. concentrationThe solution was concentrated to about 500 mL and product
9. customto crystallize
10. filtrationThe crystals were filtered

ORD record

ord-4f9ed96e1bc8440bae2a7685c3cdcb49

Source dataset

uspto-grants-2002_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06380201B1