Potassium Carbonate → HCID 131732634, compound

Participants

Reaction Steps

N-fluorobenzenesulfonimide (57.0 milligrams, 0.18 millimole) was added to a solution of 6-diethylamino-naphthalene-2-carboxaldehyde (1, 40.0 milligrams, 0.18 millimole) in 5 milliliters of anhydrous N,N-dimethylformamide under argon at −40° C. The mixture was allowed to warm up to room temperature slowly. After 3 hours, 10 milliliters of 10% K2CO3 aqueous solution was added and the product was extracted with ethyl acetate (3×50 milliliters). Solvent was removed by rotary evaporation and the residue was purified by chromatography (SiO2, 1:1 hexane/CH2Cl2) to give 2 as yellow needles (35.0 milligrams, 79%). Rf (silica gel, 1:1 Hex/CH2Cl2)=0.74; 1H NMR (400 MHz, CDCl3) δ 1.21 (t, J=7.0 Hz, 6 H), 3.45 (q, J=7.0 Hz, 4 H), 7.25 (t, J=8.8 Hz, 1 H), 7.65 (d, J=8.8 Hz, 1 H), 7.89 (dd, J=1.2 Hz, 8.8 Hz, 1 H), 8.00 (d, J=8.8 Hz, 1 H), 8.19 (s, 1 H), 10.06 (s, 1 H).

Provenance & Evidence