ChemicalBook CAS DataBase List Methyl 4-hydroxy-7-phenoxyisoquinoline-3-carboxylate

Methyl 4-hydroxy-7-phenoxyisoquinoline-3-carboxylate synthesis

8synthesis methods

Product Name:Methyl 4-hydroxy-7-phenoxyisoquinoline-3-carboxylate
CAS Number:1455091-10-7
Molecular formula:C17H13NO4
Molecular Weight:295.29

Methyl 4-hydroxy-7-phenoxyisoquinoline-3-carboxylate can be used as an intermediate in pharmaceutical synthesis. The intermediate 5-phenoxyisobenzofuran-1(3H)-one can be prepared from phenol, which is further reacted to prepare methyl 2-(chloromethyl)-4-phenoxybenzoate, which is reacted with methyl N-tosylglycinate to prepare methyl 4-hydroxy-7-phenoxyisoquinoline-3-carboxylate.

methyl2-(chloromethyl)-4-phenoxybenzoate

1455091-04-9
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2645-02-5 Synthesis

Methyl 2-(4-methylphenylsulfonamido)acetate

2645-02-5
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Methyl 4-hydroxy-7-phenoxyisoquinoline-3-carboxylate

1455091-10-7
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$53.00/250mg

Yield:1455091-10-7 72.5%

Reaction Conditions:

Stage #1:2-(chloromethyl)-4-phenoxybenzoic acid methyl ester;methyl tosylglycinate with sodium methylate;potassium carbonate;potassium iodide in N,N-dimethyl-formamide at 50; for 1 h;Inert atmosphere;
Stage #2: with sodium methylate in methanol;N,N-dimethyl-formamide at 20; for 0.5 h;

Steps:

2.3 3rd step: methyl 4-hydroxy-7-phenoxyisoquinoline-3-carboxylate (2d)
Methyl 2-(chloromethyl)-4-phenoxybenzoate (0.68 g, 2.46 mmol),N-p-toluenesulfonylglycine methyl ester (0.7 g, 2.88 mmol), potassium carbonate (0.68 g, 4.923 mmol), potassium iodide (0.16 g, 0.96 mmol), DMF was added to the reaction flask, replaced with nitrogen, and heated to 50 ° C. After reacting for 1 hour, 2 mL of methanolic sodium methoxide solution was added to room temperature and stirred for 30 min. After the reaction was completed by thin layer chromatography, 40 mL of purified water was added to the reaction mixture, and glacial acetic acid was added dropwise with stirring to adjust pH=7, suction filtration, and the filter cake was added with acetone. 4 mL was stirred for 2 hours, and suction filtered to give the title compound 2d (525 mg, 72.5%).

References:

Sichuan Kelun Botai Bio-pharmaceutical Co., Ltd.;Cai Jiaqiang;Xie Yinong;You Zejin;Song Changwei;Zhang Jichao;Li Lu;Zhang Qiaoling;Wang Yongqiang;Chen Xing;Jiao Shihu;Li Youqiang;Wang Tao;Zeng Hong;Song Hongmei;Ye Qijun;Su Donghai;Zhou Xin;Zhang Shaohua;Wang Lichun;Wang Jingyi CN108341777, 2018, A Location in patent:Paragraph 0199; 0200; 0205; 0206

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