Ethanol → HCID 59280088, compound

Participants

Reaction Conditions

Reaction Steps

2′-Fluoro-3-nitro-6′-trifluoromethyl-biphenyl-4-ylamine (754 mg, 2.51 mmol, as prepared in the previous step) was placed in a 40 mL vial equipped with a magnetic stir bar, then EtOH (20 mL) and water (5 mL) were added. Ammonium chloride (10 eq., 1.34 g, 25.1 mmol) was added as a solid, and then iron powder (5 eq., 701 mg, 12.6 mmol) was added. The vial was tightly capped and placed in a heating block where the reaction was stirred at 80° C. for 14 h. The reaction was cooled to rt, poured into water, and extracted three times with EtOAc (40 mL). The combined organic extracts were dried over anhydrous MgSO4, filtered, and the solvent was removed under reduced pressure to give 662 mg (98%) of the title compound. 1H-NMR (400 MHz, CDCl3) δ: 7.52 (d, J=7.8 Hz, 1H), 7.39 (td, J=7.9, 5.7 Hz, 1H), 7.25-7.32 (m, 1H), 6.71-6.77 (m, 1H), 6.60-6.67 (m, 2H), 3.45 (br. s., 4H).

Provenance & Evidence