3-Methoxybenzaldehyde → (E)-3-(2-(7-chloroquinolin-2-yl)ethenyl)anisole
Reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:8]=[CH:9][CH:10]=1)[CH:6]=O.[Cl:11][C:12]1[CH:21]=[C:20]2[C:15]([CH:16]=[CH:17][C:18]([CH3:22])=[N:19]2)=[CH:14][CH:13]=1>C(OC(=O)C)(=O)C>[Cl:11][C:12]1[CH:21]=[C:20]2[C:15]([CH:16]=[CH:17][C:18](/[CH:22]=[CH:6]/[C:5]3[CH:4]=[C:3]([O:2][CH3:1])[CH:10]=[CH:9][CH:8]=3)=[N:19]2)=[CH:14][CH:13]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 110 °C
Procedure
7.1 mL of 3-methoxybenzaldehyde (58 mmoles), 9.953 g of 7-chloroquinaldine (56 mmoles) and 50 mL of acetic anhydride were mixed together and heated at 110° C. for 16 hours. After hydrolysis on ice, the product was extracted with ethyl acetate, washed with 5% sodium bicarbonate and brine and partially purified by flash chromatography using 10% ethyl acetate in hexane. Recrystallisation from ether: hexane yielded the title compound.