2-chloro-7-methylquinoline synthesis

Yield: 77%

Reaction Conditions:

with trichloroisocyanuric acid;triphenylphosphine in neat (no solvent) at 160 - 170; for 18 h;Inert atmosphere;

Steps:

Preparation of 2-chloroquinoline (general procedure for preparation of α-chlorobenzopyridine):
General procedure: Ina flask (50 mL) equipped with a magnetic stirrer bar and balloon, a mixture of triphenylphosphine (1191mg, 4.54 mmol) and trichloroisocyanuric acid (360 mg, 1.55 mmol) was heated under an argonatmosphere. During the heating process, triphenylphosphine melted, and trichloroisocyanuric acidvigorously reacted at 130-140 °C to form a dark brown oil, followed by further heating for 10 min.1-Methylquinolin-2(1H)-one (242 mg, 1.50 mmol) was added to the mixture followed by heating at130-140 °C for 3 h. Then, the reaction mixture was dissolved in CH2Cl2 and basified with triethylaminefollowed by silica gel column chromatography using hexane-EtOAc (6:1) as an eluate. The product2-chloroquinoline (204 mg, 82%) was obtained.

References:

Sugimoto, Osamu;Iwasaki, Hyuma;Tanji, Ken-Ichi [Heterocycles,2015,vol. 91,# 7,p. 1445 - 1454]