4-Chlorobenzaldehyde → HCID 117702570, compound

Participants

Reaction Conditions

Reaction Steps

A round-bottomed flask was charged 5-amino-1,3-dimethylpyridin-2(1H)-one (Step 20.2) (3 g, 21.71 mmol), 4-chlorobenzaldehyde (2.348 g, 16.70 mmol) and ethyl 2,4-dioxovalerate (3.17 g, 20.04 mmol) in AcOH (50 mL) and the reaction mixture was heated up and stirred at 125° C. for 1 hr. The reaction mixture was concentrated under reduced pressure, quenched with a saturated aq. NaHCO3 solution, extracted with EtOAc. The organic layer was discarded and the aq. phase was adjusted to pH 1-2, extracted EtOAc. The combined organic layers were dried over Na2SO4 and concentrated under reduced pressure to afford the title product (3.82 g, 8.71 mmol, 52% yield) as a black solid. tR: 3.54 min (HPLC 1); tR: 0.75 min (LC-MS 2); ESI-MS: 373 [M+H]+ (LC-MS 2).

Provenance & Evidence