ChemicalBook CAS DataBase List Oxolinic acid

Oxolinic acid synthesis

9synthesis methods

Product Name:Oxolinic acid
CAS Number:14698-29-4
Molecular formula:C13H11NO5
Molecular Weight:261.23

Oxolinic acid, 5-ethyl-5,8-dihydro-8-oxo-1-dioxolo[4,5-g]-quinolin- 7-carboxylic acid (33.2.9), is basically synthesized by the same synthetic scheme as nalidixic acid, although it uses 3,4-methylendioxyanyline (33.2.6) as the starting aromatic amine component, and not the 2-amino-6-methylpyridine used to make nalidixic acid. This compound is obtained by hydrogenation to 3,4-methylendioxy-1-nitrobenzene (33.2.5), which is in turn synthesized by nitrating 1,2-methylendioxybenzene with nitric acid. The resulting 3,4-methylendioxyaniline (33.2.6) is then reacted with ethoxymethylenmalonic ester to make the substitution product (33.2.7), which when heated cyclizes to ethyl ester of 4-hydroxy-6,7-methylendioxyquinolin-3-carboxylic acid (33.2.8). Hydrolyzis of this with a base in dimethylformamide and direct treating of the obtained product with ethyl iodide gives the desired oxolinic acid.

diethyl [[N-ethyl-3,4-(methylenedioxy)anilino]methylene]malonate

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Yield:14698-29-4 92.4%

Reaction Conditions:

Stage #1: Ethyl α-ethoxycarbonyl-β-N-(5-benzodioxolyl)-N-ethylaminoacrylatewith sulfuric acid;acetic anhydride at 80 - 130; for 4 h;
Stage #2: in water at 90; for 3 h;

Steps:

1-5 Example 1

General procedure: N-ethyl-3,4-(methylenedioxy)aniline (Compound I 82.5 g, 0.5 mol)add toDimethylammonium methylene malonate(Compound II 118g, 0.55 mol),After heating to 140 ° C for 3 hours, the temperature was lowered to 100 ° C.Add acetic anhydride (76.5g, 0.75mol), and then cool to 80 ° C,Slowly add concentrated sulfuric acid (50g, 0.5mol), after the addition,After heating to 130 ° C for 4 hours, after the reaction is completed, the temperature is lowered to 90 ° C.Add 530g of water, hydrolyze for 3 hours, then reduce to room temperature, filter, refine, and dry.Get oxolinic acid.

References:

CN109651386,2019,A Location in patent:Paragraph 0025-0028

425-75-2 Synthesis