Sodium Iodide → HCID 22227049, compound

Participants

Reaction Steps

4-Amino-3-nitrophenol (5.00 g, 32.4 mMol), Cs2CO3 (22.8 g, 70 mMol), sodium iodide (476 mg, 3.20 mMol) and 2-picolyl chloride hydrochloride (11.2 g, 35 mMol) were added to 20 mL of anhydrous DMF under an atmosphere of dry N2. The reaction mixture was stirred overnight at ambient temperature. The reaction mixture is then poured into water. The precipitate was collected via suction filtration. The precipitate was partitioned between DCM and 1.0 N aqueous NaOH. The organic layer was washed 2 more times with 1 N aqueous NaOH to remove any unreacted phenol. The organic layer was then washed with brine, dried over Na2SO4, filtered and concentrated under vacuum to give 7.7 g of a dark red solid. The solid was chromatographed on flash silica gel eluting with EtOAc/DCM (2080) to give 3.7 g of the title compound 47A as an orange solid.

Provenance & Evidence