Ammonium Chloride → 2,6-Dimethylquinolin-5-amine

To a solution of 2,6-dimethyl-5-nitro-quinoline (192 mg, 0.95 mmol) in ethanol (9.3 mL) and water (4.7 mL) were added iron powder (280 mg, 5.0 mmol) and NH4Cl 280 mg, 5.2 mmol). The mixture was heated at reflux for 2 h, then cooled filtered. The filtrate was concentrated under reduced pressure, and the aqueous residue was extracted with ethyl acetate. The combined extracts were washed with water and brine, dried over Na2SO4, filtered and concentrated to dryness under reduced pressure. Purification of the residue by flash column (hexane/ethyl acetate gradient) gave 2,6-dimethyl-quinolin-5-ylamine (120 mg, 73%).

1. temperatureThe mixture was heated
2. temperatureat reflux for 2 h
3. temperaturecooled
4. filtrationfiltered
5. concentrationThe filtrate was concentrated under reduced pressure
6. extractionthe aqueous residue was extracted with ethyl acetate
7. washThe combined extracts were washed with water and brine
8. dry with materialdried over Na2SO4
9. filtrationfiltered
10. concentrationconcentrated to dryness under reduced pressure
11. customPurification of the residue by flash column (hexane/ethyl acetate gradient)

ORD-Eintrag

ord-cab1453c767c4b8e92c962c81c382901

Quelldatensatz

uspto-grants-2013_05

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US08435990B2