Potassium Carbonate → 2-Nitroaniline

Participants

Reaction Steps

2,4,5-tri-fluoronitrobenzene (2.864 g, 0.016 mol), K2CO3 (2.236 g, 0.0161 mol) and (5-fluoropyridin-3yl)methanamine TFA salt (1.02 g, 50% LC-MS) were dissolved in THF (25 mL) and stirred at room temperature for 16 hours. The reaction mixture was then diluted with EtOAc (100 mL) and washed with H2O. The organic phase was dried and concentrated under vacuum to give the ortho-substitution product, 4,5-difluoro-N-(5-fluoropyridin-3-yl) methyl)-2-nitroaniline as a yellow solid. 1H NMR (400 MHz, DMSO-d6), δ: 8.72 (br, 1H), 8.43 (s, 1H), 8.39 (s, 1H), 8.15 (dd, J=10 Hz, 8.8 Hz, 1H), 7.65 (d, J=9.2 Hz, 1H), 6.83 (dd, J=12.8 Hz, 7.8 Hz, 1H), 4.71 (s, 2H). MS (M+1): 284

Provenance & Evidence