Hydrochloric Acid → 4-Fluoro-2-methyl-6-nitroaniline

Participants

Reaction Steps

A mixture of N-(4-fluoro-2-methyl-6-nitrophenyl)acetamide (20 g, crude), concentrated hydrochloric acid (100 mL), and H2O (100 mL) was refluxed overnight. The reaction mixture was subsequently extracted with DCM. The organic phase was washed with aqueous NaHCO3 until the pH of the aqueous layer was >7. The organic phase was washed with water and dried over Na2SO4. The solvent was evaporated to give the title compound as a solid (5.5 g, 34%). 1H NMR (400 MHz, CDCl3) δ ppm 7.68 (1H, dd, J1=2.8 Hz, J2=9.2 Hz), 7.05 (1H, dd, J1=2.8 Hz, J2=8.0 Hz), 5.99 (2H, s), 2.19 (3H, s).

Provenance & Evidence