4-(Dimethylamino)Benzaldehyde → HCID 54197884, compound

Participants

Reaction Steps

A solution of 4.8 g of 1-(2,3-dihydro-1H-inden-5-yl)ethanone 5; 30 mmoles), 4.5 g of p-dimethylaminobenzaldehyde (30 mmoles), and 1.32 g of sodium hydroxide in 40 ml of methanol was stirred under nitrogen at room temperature for 48 hr. The reaction mixture was cooled in an ice bath and the precipitated solid 3-[4-(dimethylamino)phenyl]-1-(2,3-dihydro-1H-inden-5-yl)-2-propen-1-one was collected by filtration and washed with cold methanol. Yield: 4.2 g (48%); m.p. 106° to 108°. λmax (EtOH): 416 nm (ε=34,700); 272 nm (15,400). Calcd for C20H21NO: C, 82.44; H, 7.26; N, 4.81. Found: C, 82.19, 82.12; H, 7.21, 7.24; N, 4.70, 4.67.

Provenance & Evidence