ChemicalBook CAS DataBase List 4-Chloro-7-methoxyquinoline

4-Chloro-7-methoxyquinoline synthesis

8synthesis methods

Product Name:4-Chloro-7-methoxyquinoline
CAS Number:68500-37-8
Molecular formula:C10H8ClNO
Molecular Weight:193.63

82121-05-9 Synthesis

82121-05-9
170 suppliers
$58.00/5g

68500-37-8
198 suppliers
$18.00/250mg

Yield:68500-37-8 88%

Reaction Conditions:

with trichlorophosphate for 3 h;Heating;

Steps:

5.4 4-Chloro-7-methoxyquinoline (7)

A mixture of 7-methoxyquinolin-4(1H)-one 6 (10mmol) and phosphorous oxychloride (30mL) was heated for 3h. Most of phosphorous oxychloride was removed by evaporation under reduced pressure, and the residue was poured into ice water. Then, the mixture was made alkaline with ammonium hydroxide; the precipitate formed was collected by filtration, washed well with water and dried in a vacuum; and compound 7 was obtained as white solid (1.7g, 88%). ESI-MS m/z 194 [M+H]⁺. ¹H NMR (300MHz, CDCl₃): δ 8.67 (1H, d, J= 4.8Hz, ArH), 8.09 (1H, d, J= 9.0Hz, ArH), 7.42 (1H, d, J= 2.4Hz, ArH), 7.33 (1H, d, J= 4.8Hz, ArH), 7.28 (1H, dd, J=9.0Hz, J=2.4Hz, ArH), 3.97 (3H, s, CH₃). ¹³C NMR (75MHz, CDCl₃) δ 161.3, 151.0, 150.2, 142.4, 125.3, 121.7, 120.8, 119.3, 107.7, 55.9.

References:

Li, Shangze;Hu, Lihua;Li, Jianru;Zhu, Jiongchang;Zeng, Feng;Huang, Qiuhua;Qiu, Liqin;Du, Runlei;Cao, Rihui [European Journal of Medicinal Chemistry,2019,vol. 162,p. 666 - 678]

82121-05-9 Synthesis

82121-05-9
170 suppliers
$58.00/5g

68500-37-8
198 suppliers
$18.00/250mg

References