反应详情

Sodium hydride (555 w/w suspension in oil; 0.268 g) was added portionwise to a stirred suspension of 1,2-dihydro-2-oxoquinoline-3-carbaldehyde (1 g) in dimethylformamide (10 ml) which had been cooled in an ice bath. The mixture was allowed to warm to ambient temperature and was then heated to 60° C. for 1 hour. The mixture was recooled in an ice bath and methyl iodide (0.41 ml) was added. Dimethylformamide (50 ml) was added and the mixture was stirred at ambient temperature for 16 hours. The mixture was poured into water (50 ml) and extracted with methylene chloride (3×50 ml). The combined extracts were washed with water (50 ml) and evaporated. The residue was triturated under diethyl ether to give 1,2-dihydro-1-methyl-2-oxoquinoline-3-carbaldehyde as a pale yellow solid (0.81 g, 74%).

1. temperaturehad been cooled in an ice bath
2. temperaturewas then heated to 60° C. for 1 hour
3. customThe mixture was recooled in an ice bath
4. extractionextracted with methylene chloride (3×50 ml)
5. washThe combined extracts were washed with water (50 ml)
6. customevaporated
7. customThe residue was triturated under diethyl ether