ChemicalBook CAS DataBase List n-(4-Chloro-3-cyano-7-ethoxy-6-quinolinyl) acetamide

n-(4-Chloro-3-cyano-7-ethoxy-6-quinolinyl) acetamide synthesis

9synthesis methods

Product Name:n-(4-Chloro-3-cyano-7-ethoxy-6-quinolinyl) acetamide
CAS Number:848133-76-6
Molecular formula:C14H12ClN3O2
Molecular Weight:289.72

N-(4-Chloro-3-cyano-7-ethoxy-6-quinolinyl)acetamide is used in synthesis of an antitumor agent, neratinib (N390090). The mixtrue of N-(3-cyano-7-ethoxy-4-hydroxyquinolin-6-yl)acetamide, diethylene glycol dimethyl ether and POCl3 was stirred at 85° C. for 4-4.5 h. The reaction mixture was slowly poured into ice-water and stirred for 1 h to give N-(4-Chloro-3-cyano-7-ethoxy-6-quinolinyl) acetamide.

Acetamide, N-(3-cyano-7-ethoxy-4-hydroxy-6-quinolinyl)-

848133-75-5
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n-(4-Chloro-3-cyano-7-ethoxy-6-quinolinyl) acetamide

848133-76-6
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$8.00/250mg

Yield:848133-76-6 93.6%

Reaction Conditions:

with trichlorophosphate in diethylene glycol dimethyl ether at 85; for 4 - 4.5 h;Product distribution / selectivity;

Steps:

29
Example 29 6-Acetylamido-7-ethoxy-3-cyano-4-chloro-quinoline (a compound of formula A, W=Cl) The title compound of example 28 (23 g, 0.0857 mol) was added to diethylene glycol dimethyl ether (400 mL), and then POCl₃ (24 mL, 0.257 mol) was added thereto and stirred at 85° C. for 4-4.5 h. The reaction mixture was slowly poured into two volumes of ice-water and stirred for 1 h to precipitate a yellow powder. The precipitate was filtered and washed with water and then washed with a small amount of diethylene glycol dimethyl ether, and dried at 40° C. to give 23 g of the title compound with a yield of 93.6%.

References:

Shanghai Institute of Materia Medica, Chinese Academy of Sciences;Topharman Shangai Co., Ltd. US2011/263860, 2011, A1 Location in patent:Page/Page column 8

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