8-Chloro-2,3-dimethyl-quinolin-4-ol synthesis

Yield:-

Reaction Conditions:

Stage #1: 2-acetylpropanoic acid ethyl ester;o-chloroanilinewith norepinephrine at 140; for 23 h;
Stage #2: with sodium hydroxide in water;

Steps:

39 8-Chloro-N-(2,5-di-4-morpholinylphenyl)-2,3-dimethyl-4-quinolinamine

Example 39 8-Chloro-N-(2,5-di-4-morpholinylphenyl)-2,3-dimethyl-4-quinolinamine A mixture of 2-chlorobenzenamine (5.342 g, 41.9 mmol) and ethyl 2-methyl-3-oxobutanoate (12.1 mL, 83.7 mmol) in 16 g PPA was heated to 140° C. for 23 h then equilibrated to rt. Approximately 200 mL of 5% aq. sodium hydroxide solution was added and the resulting pink precipitate collected by filtration, rinsing with water. The pink solid was dried in a vacuum dessicator over P₂O₅. After several hours, the solid was suspended in hot EtOAc and the solid collected by filtration. The resulting colorless solid was dried under reduced pressure. Mass Spectrum (ESI) m/e=208.0 (M+1).

References:

US2010/331293,2010,A1 Location in patent:Page/Page column 45