(2E)-1-(4-aminophenyl)-3-[4-(dimethylamino)phenyl]prop-2-en-1-one

Preparation

Synthesis of ADAB: 1-(4-aminophenyl)-3-(4-(dimethylamino)phenyl)prop-2-en-1-one (ADAB):
4-aminoacetophenone( 1 g, 6.7 mmol) was suspended in ethanol (20 mL), to the suspension 40% of NaOH and 4-dimethylaminobenzaldeyde(0.904 g, 6.7 mmol) were added and stir this reaction mixture at RT for 16h. After completion of the reaction, the reaction mixture was poured into the 100 mL of ice water and P H is adjusted to 1 by drop wise adding of dil. HCl. The reaction mixture was filtered; the filtrate was neutralized with 5% NaHCO3 and subsequently extracted with CH2Cl2. The organic fraction was concentrated in vacuum under reduced pressure. Yield 1.569 g (86%).
1H NMR (400 MHz, CDCl3) δ, 8.10 (dd, J = 15.6, 8.5 Hz, 2H), 7.98 – 7.69 (m, 1H), 7.59 (dd, J = 8.8, 1.9 Hz, 1H), 7.42 (ddd, J = 15.4, 14.6, 6.7 Hz, 2H), 7.20 – 6.89 (m, 2H), 6.75 (dd, J = 15.5, 8.8 Hz, 2H), 3.26 – 2.91 (m, 6H), 1.64 (s, 2H), 13C NMR (101 MHz, CDCl3) δ 161.34 – 161.14 (m), 130.85 (s), 129.58 (s), 121.45 – 121.25 (m), 111.86 (s), 77.35 (s), 77.03 (s), 76.71 (s), 40.17 (s).