Dimethyl malonate → HCID 59804279, compound

Participants

Reaction Conditions

Reaction Steps

To a suspension of 60% of NaH in mineral oil (300 mg, 7.41 mmol) in DMSO (2.5 mL) is added dimethyl malonate (851 μL, 7.41 mmol). The mixture is heated to 60° C. for 10 minutes and then cooled to ambient temperature before (4-fluoro-3-nitro-phenyl)-(3-nitro-phenyl)-amine (686 mg, 2.47 mmol) is added. The resulting mixture is heated to 60° C. for 3 hours and quenched with saturated aqueous NH4Cl solution. The mixture is extracted with EtOAc, washed with brine, dried over MgSO4, and concentrated. The crude product is purified by column chromatography (EtOAc/Hexane, gradient) to give the desired product: 1H NMR (400 MHz, CDCl3) δ. 7.94 (s, 1 H), 7.88 (d, 1 H), 7.70 (d, 1 H), 7.51-7.47 (m, 1 H), 7.44-7.40 (m, 2 H); 7.32-7.28 (m, 1H), 5.27 (s, 1H), 3.83 (s, 6H); LC-MS: 390.3 (MH+).

Provenance & Evidence