Acetic acid ethanol → HCID 178519433, compound

Participants

Reaction Conditions

Reaction Steps

To a yellow-orange solution of N-(4-benzyl-2-nitrophenyl)-4-(dimethoxymethyl)-2-fluorobenzamide (0.466 g, 1.1 mmol) in 5 mL 3:2 AcOH/EtOH was added iron powder—325 mesh (0.078 mL, 11 mmol). The reaction was fitted with a reflux condensor and was stirred rapidly at 120° C. bath. The reaction became a nearly solid mass after 10 min, and 3 mL 2:1 AcOH/EtOH was added to promote stirring. After 3 h, the mixture was bright yellow. The reaction was diluted with water, EtOAc, and brine, and the layers were separated. The aqueous layer was extracted 2× EtOAc, and the combined organics were washed 2×1N NaOH and 1× brine, dried over sodium sulfate, filtered, and concentrated to an orange oil. The material was purified by silica gel chromatography, ISCO, 40 g, 0-40% 90/10 DCM/MeOH in DCM to give title compound. MS (ESI) m/z: Calculated: 332.1; Observed: 333.1 (M++1).

Provenance & Evidence