O-Xylene → 3-(2-(7-Chloroquinolin-2-yl)vinyl)benzaldehyde

Participants

Reaction Steps

To 15 liters of xylene preheated to 100° were added sequentially 7-chloroquinaldine (3 kg, 16.9 moles; see C. M. Leir, J. Org. Chem., 42, 911-913 (1977)), isophthalaldehyde (3.4 kg, 25.3 moles), and acetic anhydride (4.69 liters, 5.07 kg, 49.7 moles). The mixture was heated at reflux for about 8 to 9 hours and then cooled to room temperature. Hexane (16 liters) was added and the resultant precipitate was collected by filtration. Recrystallization from ethyl acetate yielded pure title compound (67%).

Provenance & Evidence