1-(chloroacetyl)-6-methyl-1,2,3,4-tetrahydroquinoline synthesis

Yield:57368-83-9 94%

Reaction Conditions:

with triethylamine in dichloromethane at 25;Inert atmosphere;

Steps:

5.1.3. General method B (GMB) for the preparation of 2-chloro-1-(3,4-dihydro-2H-quinolin-1-yl)-ethanone, amide, and indoline derivatives

General procedure: To a solution of substituted 1,2,3,4-tetrahydroquinoline, morpholine,aniline, or indoline in dichloromethane was added triethylamineand chloroacetyl chloride in ice bath. The solution was stirred at 25 Cfor 2.5 h to 2 d and then washed with 1.0 N HCl(aq) and brine. Theorganic layer was dried with MgSO4(s), filtered, and concentrated toafford a product which was directly used to next step without furtherpurification. In some examples, the desired product was purified bychromatographic separation or recrystallization.

References:

Lin, Shu-Yu;Tien, Ya-Wen;Ke, Yi-Yu;Chang, Yung-Chiao;Chang, Hsiao-Fu;Ou, Li-Chin;Law, Ping-Yee;Xi, Jing-Hua;Tao, Pao-Luh;Loh, Horace H.;Chao, Yu-Sheng;Shih, Chuan;Chen, Chiung-Tong;Yeh, Shiu-Hwa;Ueng, Shau-Hua [Bioorganic Chemistry,2022,vol. 128,art. no. 105905]