2-chloro-7-methylquinoline synthesis
- Product Name:2-chloro-7-methylquinoline
- CAS Number:4295-12-9
- Molecular formula:C10H8ClN
- Molecular Weight:177.63
67200-70-8
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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]
![Ethanamine, N-[(3,5-dichlorophenyl)methylene]-2,2-diethoxy-](/CAS/20210305/GIF/1000210-73-0.gif)
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