Ammonium Chloride → HCID 58154634, compound

Temperature

90 °C

Crude 2-(3-fluoro-5-(trifluoromethyl)phenyl)-8-nitroquinoline (2.78 mmol) was taken up in isopropyl alcohol (120 mL) and ammonium chloride (150 mg, 2.8 mmol) in water (20 mL) was added. The mixture was heated to 90° C., iron powder (550 mg, 9.85 mmol) was added and the reaction was continued stirring at 90° C. 18 hours. The reaction mixture was filtered over celite and the celite cake was washed with ethyl acetate (150 mL). The filtrate was concentrated and the residue was taken up in 1N aqueous NaOH (80 mL) and extracted with ethyl acetate (3×25 mL). The organic layers were combined, washed with brine, dried (MgSO4), and concentrated. The crude material was purified by flash chromatography (a gradient of 0 to 100% ethyl acetate in pentane) to obtain 2-(3-fluoro-5-(trifluoromethyl)phenyl)quinolin-8-amine (0.42 g, 1.37 mmol, 49% yield over two steps).

1. custom18 hours
2. filtrationThe reaction mixture was filtered over celite
3. washthe celite cake was washed with ethyl acetate (150 mL)
4. concentrationThe filtrate was concentrated
5. extractionextracted with ethyl acetate (3×25 mL)
6. washwashed with brine
7. dry with materialdried (MgSO4)
8. concentrationconcentrated
9. customThe crude material was purified by flash chromatography (a gradient of 0 to 100% ethyl acetate in pentane)

ORD record

ord-96c9c101a5a0406cb772f11204c2ec42

Source dataset

uspto-grants-2014_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08685970B2