Oxalyl chloride → HCID 58415379, compound

Participants

Reaction Steps

2-Fluoro-4-formylbenzoic acid (0.300 g, 1.78 mmol) was slurried in 10 mL DCM and catalytic DMF was added, followed by oxalyl chloride (0.317 mL, 3.57 mmol). The reaction was allowed to stir several h. Upon consumption of the acid, the reaction was concentrated in vacuo and diluted with 7 mL THF. 4-Benzyl-2-nitrobenzenamine (0.611 g, 2.68 mmol) and diisopropylethylamine (0.622 mL, 3.57 mmol) was added as a solution in 5 mL THF. The reaction was allowed to stir overnight and worked up with EtOAc/saturated sodium bicarbonate, dried over sodium sulfate, filtered, and concentrated. The residue was treated with p-toluenesulfonic acid monohydrate (0.170 g, 0.892 mmol) and MeOH. After 1 h, the mixture was concentrated and adsorbed onto silica gel and purified by chromatography to give N-(4-benzyl-2-nitrophenyl)-4-(dimethoxymethyl)-2-fluorobenzamide. MS (ESI) m/z: Calculated: 424.1; Observed: 425.2 (M++1).

Provenance & Evidence