Nitric Acid → N-(4-fluoro-2-methyl-6-nitrophenyl)acetamide
Reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9](=[O:11])[CH3:10])=[C:4]([CH3:12])[CH:3]=1.[N+:13]([O-])([OH:15])=[O:14]>O(C(C)=O)C(C)=O>[F:1][C:2]1[CH:7]=[C:6]([N+:13]([O-:15])=[O:14])[C:5]([NH:8][C:9](=[O:11])[CH3:10])=[C:4]([CH3:12])[CH:3]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
To a mixture of N-(4-fluoro-2-methylphenyl)acetamide (19 g, 113.1 mmol, 1 eq) and (CH3CO)2O (190 mL) was added HNO3 (11.4 mL, 1.0 eq) dropwise at 0° C. The reaction mixture was allowed to warm to RT overnight and was subsequently poured onto ice and 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 then dried over Na2SO4. The solvent was evaporated to give the title compound as a crude solid (20 g, 84%). 1H NMR (400 MHz, DMSO-d6) δ ppm 9.82 (1H, s), 7.71 (1H, dd, J1=2.8 Hz, J2=8.0 Hz), 7.56 (1H, dd, J1=2.8 Hz, J2=9.2 Hz), 2.32 (3H, s), 2.02 (3H, s).