Hydrochloric Acid → 6-Chloro-3-methylquinolin-5-amine

Temperature

50 °C

To a solution of 6-chloro-3-methyl-5-nitroquinoline (6.70 g, 30.1 mmol) in methanol (45 mL) was added iron powder (5.55 g, 99.3 mmol), followed by careful addition of a concentrated aqueous HCl solution (15.6 mL). The resulting reaction mixture was heated for 1 h at 50° C. and concentrated at reduced pressure using a rotary evaporator. The residue was dissolved in water and basified (pH=9) using a 33% aqueous ammonia solution. The resulting brown suspension was extracted twice with EtOAc and the combined organic layers were washed with brine, dried over Na2SO4, filtered and concentrated at reduced pressure to afford the title compound as a brown solid (4.92 g, 25.5 mmol, 85%). 1H NMR (400 MHz, CDCl3, 298 K): δ=8.75 (s, 1H), 7.93 (s, 1H), 7.53 (d, J=9.0 Hz, 1H), 7.50 (d, J=9.0 Hz, 1H), 2.56 (s, 3H). MS (ES+): 193 (M(C10H935ClN2)+H)+.

1. customThe resulting reaction mixture
2. concentrationconcentrated at reduced pressure
3. customa rotary evaporator
4. dissolutionThe residue was dissolved in water
5. extractionThe resulting brown suspension was extracted twice with EtOAc
6. washthe combined organic layers were washed with brine
7. dry with materialdried over Na2SO4
8. filtrationfiltered
9. concentrationconcentrated at reduced pressure

ORD record

ord-895598c2c8614e308d5de8083ea2bdda

Source dataset

uspto-grants-2010_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07781438B2