Sodium Hydroxide → (E)-7((5-Methyl-1H-imidazol-4-yl)methylene)-6,7-dihydroquinolin-8(5H)-one

Participants

Reaction Steps

A solution of (3) (0.990 g, 6.73 mmol) and 5-methyl-1H-imidazole-4-carbaldehyde (0.890 g, 8.05 mmol) in 40% sulfuric acid (10 mL) was heated at 110° C. for 16 h. The reaction was cooled to rt. Crushed ice was added and the mixture was stirred vigorously, while NaOH(s) was added carefully. At pH ˜6 the product precipitated from solution. The mixture was stirred for 30 m at room temperature, and filtered to isolate (E)-7-((5-Methyl-1H-imidazol-4-yl)methylene)-6,7-dihydroquinolin-8(5H)-one (4) as a yellow solid, 1.39 gram (5.81 mmol, 86% yield).

Provenance & Evidence