ChemicalBook CAS DataBase List 4-chloro-6,7-dimethoxyquinoline

4-chloro-6,7-dimethoxyquinoline synthesis

10synthesis methods

Product Name:4-chloro-6,7-dimethoxyquinoline
CAS Number:35654-56-9
Molecular formula:C11H10ClNO2
Molecular Weight:223.66

With 3,4-dimethoxyaniline is raw material, obtains aniline compound through nitrification, iron powder reducing, then with Ethyl chloroformate, in Feldalat NM condition cyclization, prepares 4-hydroxyquinoline compounds, after through three Chlorethoxyfos chloro obtains 4-chloro-6,7-dimethoxy-quinoline.
4-chloro-6,7-dimethoxyquinoline synthesis

4-chloro-6,7-dimethoxyquinoline synthesis

13425-93-9
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$6.00/1g

35654-56-9
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$13.00/1g

Yield:35654-56-9 91.4%

Reaction Conditions:

with trichlorophosphate in acetonitrile at 85; for 2 h;

Steps:

1.5. General procedure for preparation of(4)
Phosphorus oxychloride (200 mL, 4 v/w) was slowly added into a stirred solution of the intermediate3(50.0 g, 0.24 mol) in acetonitrile (500 mL, 10 v/w), and then was heated at 85^oCfor 2 h. After cooling to r.t., the phosphorus oxychloride was removed under reduced pressure. The residue was poured into ice water and adjusted to pH 12 with 10NNaOH. The precipitates were collected by filtration and the filter cake was washed with water until the filtrate was nearly neutral to give compound4as a pale yellow solid in 91.4% yield. MS (ESI) m/z: 224.13[M+H]⁺.

References:

Xu, Qiaoling;Dai, Baozhu;Li, Zhiwei;Xu, Le;Yang, Di;Gong, Ping;Hou, Yunlei;Liu, Yajing [Bioorganic and Medicinal Chemistry Letters,2019,vol. 29,# 19,art. no. 126630] Location in patent:supporting information

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