4-Chlorobenzaldehyde → 5-(2-(4-chlorophenyl)-4-hydroxy-5-oxo-3-propionyl-2,5-dihydro-1H-pyrrol-1-yl)-1,3-dimethylpyridin-2(1H)-one

Participants

Reaction Conditions

Reaction Steps

A mixture of 5-amino-1,3-dimethylpyridin-2(1H)-one (Step 20.2) (1.77 g, 12.78 mmol), 4-chlorobenzaldehyde (1.63 g, 11.62 mmol) and ethyl 4-cyclopropyl-2,4-dioxobutanoate (2 g, 11.62 mmol) in acetic acid (10 mL) was stirred for 2 h at 100° C. The reaction mixture was concentrated, diluted with CH2Cl2/1 N NaOH, and extracted with CH2Cl2. The combined organic extracts were discarded. The aqueous layer was acidified to pH 3 with 6 N HCl and extracted twice with CH2Cl2. The combined organic extracts were dried (Na2SO4) and concentrated to afford 3.06 g of the title compound as a beige foam. tR. 0.83 min (LC-MS 2); ESI-MS: 387.0 [M+H]+ (LC-MS 2).

Provenance & Evidence