ChemicalBook CAS DataBase List Amodiaquine

Amodiaquine synthesis

5synthesis methods

Product Name:Amodiaquine
CAS Number:86-42-0
Molecular formula:C20H22ClN3O
Molecular Weight:355.86

Amodiaquin, 4-[(7-chloro-4-quinilyl)amino]-α-diethylmaino-o-cresol (37.1.1.21), is made by reacting 4,7-dichloroquineoline (37.1.1.1) with 4-aminophenol to make 7-chloro-4-(4-hydroxyphenylamino)-quiniline (37.1.1.20), which then undergoes an aminomethylation reaction using formaldehyde and diethylamine, giving amodiaquin.

86-98-6 Synthesis

86-98-6
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123-30-8 Synthesis

123-30-8
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109-89-7
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86-42-0
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Yield:-

Reaction Conditions:

Stage #1: 4,7-dichloroquinoline;4-amino-phenolwith acetic acid in water at 20 - 110; for 1 h;
Stage #2: diethylaminewith formaldehyd in water;acetic acid at 50; for 4 h;
Stage #3: with hydrogenchloride in water;

Steps:

1

To a mixture of 4-aminophenol (11.4 grams, 0.104 mol) and 4,7- dichloroquinoline (19.8 grams, 0.10 mol), acetic acid was added (60 ml, 3.0 volumes w/v relative to 4,7-dichloroquinoline) with stirring at room temperature and the resulting mixture was heated with stirring at 110°C for about one hour. The mixture was cooled to 20°C and formaldehyde (14.06 grams of a 32% aqueous solution, 0.150 mol, 1.5 mol eq) and diethylamine (10.95 grams, 0.150 mol, 1.5 mol eq were sequentially added to the same reaction vessel). The reaction mixture was then heated and reaction occurred at 50°C for four hours. The mixture was cooled in an ice water bath and 22 mL of 37% aqueous hydrochloric acid solution (containing 0.264 mol of HC1) was added at a rate so that the internal temperature did not exceed 40°C. Stirring was continued for an additional 2 hours to complete the precipitation of the desired product as yellow crystals The precipitated crystals were collected by filtration and dried at room temperature to a constant weight to obtain 42.7 grams of amodiaquine dihydrochloride dihydrate (92% yield) in a purity of greater than 99% as determined by HPLC analysis.

References:

WO2013/138200,2013,A1 Location in patent:Paragraph 0073; 0074