Acetic Acid → 3-Quinolinecarbonitrile, 7-ethoxy-1,4-dihydro-6-methoxy-4-oxo-

Participants

Reaction Conditions

Reaction Steps

Added 54.0 ml (135 mmol) n-butyl lithium to 150 ml THF and chilled to −78° C. under N2. Added dropwise over 20 minutes 7.05 ml (135 mmol) acetonitrile in 200 ml THF. Stirred 15 minutes and added a solution of 17.99 g (64.2 mmol) methyl 4-ethoxy-5-methoxy-2-(dimethylaminomethyleneamino)benzoate in 150 ml THF dropwise over 20 minutes. Let stir for 0.5 hour at −78° C. Added 11.0 ml (193 mmol) acetic acid and warmed gradually to 25° C. After 2.5 hours, stripped solvent, slurried residue with water, collected solids and dried in vacuo, giving 13.025 g of yellow solid: mass spectrum (electrospray m/e): M+H=245.2.

Provenance & Evidence