16172-03-5

Basic information

• Product Name: OXOLINIC ACID IMPURITY B
• Synonyms: OXOLINIC ACID IMPURITY B;Ethyl 5-ethyl-8-oxo-5,8-dihydro-1,3-dioxolo[4,5-g]quinoline-7-carboxylate
• CAS NO: 16172-03-5
• Molecular Formula: C₁₅H₁₅NO₅
• Molecular Weight: 261.23014
• Mol File: 16172-03-5.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: OXOLINIC ACID IMPURITY B(CAS DataBase Reference)
• NIST Chemistry Reference: OXOLINIC ACID IMPURITY B(16172-03-5)
• EPA Substance Registry System: OXOLINIC ACID IMPURITY B(16172-03-5)

Safety Data

• Hazardous Substances Data: 16172-03-5(Hazardous Substances Data)

Usage

Uses

As OXOLINIC ACID IMPURITY B is a harmful impurity, its primary use is in the context of quality control and safety monitoring in the pharmaceutical industry. It is not intended for direct application in any therapeutic or industrial process.
Used in Pharmaceutical Industry:
OXOLINIC ACID IMPURITY B is used as a quality control parameter for ensuring the safety and efficacy of oxolinic acid-containing medications. It is monitored and controlled to adhere to the maximum limits established by regulatory agencies such as the US Food and Drug Administration (FDA) and the European Medicines Agency (EMA) to safeguard public health.

Upstream product

• 32953-23-4 Ethyl α-ethoxycarbonyl-β-N-(5-benzodioxolyl)-N-ethylaminoacrylate 
• 6296-99-7 diethyl aminomethylenemalonate 
• 32953-14-3 N-ethyl-3,4-(methylenedioxy)aniline 
• 87-13-8 diethyl 2-ethoxymethylenemalonate 
• 33331-61-2 4-ethoxy-3-ethoxycarbonyl-6,7-methylenedioxyquinoline 
• 75-03-6 ethyl iodide 
• 57385-14-5 1,3-dioxolo<4,5-g><3,1>benzoxazine-6,8(5H)dione 
• 66176-21-4 4,5-methylenedioxyanthranilic acid hydrochloride 
• 32953-32-5 8-chloro-7-ethoxycarbonyl-5-ethyl-[1,3]dioxolo[4,5-g]quinolinium; iodide 
• 114954-61-9 ethyl 4-aza-5-dimethylamino-2-ethoxycarbonyl-2,4-pentadienoate 
• 16171-98-5 3-ethoxycarbonyl-6,7-methylenedioxy-4-quinolone 
• 78-40-0 triethyl phosphate 
• 60792-23-6 7-ethoxycarbonyl-5-ethyl-8-sulfo-[1,3]dioxolo[4,5-g]quinolinium betaine 
• 50332-64-4 2H-6,7-methylenedioxy-3,1-benzoxazine-2,4-(1-ethyl)-dione 

Downstream Products

• 14698-29-4 oxolinic Acid 
• 19658-59-4 5-ethyl-8-oxo-5,8-dihydro-[1,3]-dioxolo[4,5-g]quinoline-7-carbonyl chloride 
• 51624-54-5 9-amino-5-ethyl-8-oxo-5,8-dihydro-[1,3]dioxolo[4,5-g]quinolin-7-carboxylic acid 

Relevant articles and documents

Microwave-assisted synthesis of quinolone derivatives and related compounds

(Chemical Equation Presented) The Gould-Jacob type of reaction for the synthesis of ethyl 5-ethyl-8-oxo-5,8-dihydro-[1,3]-dioxolo[ 4,5-g]quinoline-7- carboxylate 4 has been carried out conventionally by the condensation between N-ethyl-3,4-methylenedioxyaniline 1 and diethyl ethoxymethylenemalonate 2 gave the unsaturated ester 3 and thermal cyclization in refluxing diphenyl oxide gave quinolone ethyl ester 4 and the results obtained were compared with single step microwave irradiation under solvent free conditions for the synthesis of 4. The esters on basic hydrolysis formed free acid 5, which, upon treatment with thionyl chloride gave the acid chloride 6. Treatment of acid chloride with o-phenylenediamine, hydrazine hydrate, ammonia, urea, and thiourea gave the amides (7-11). CS2 treatment in presence of KOH on 8 gave 12. We prepared 7-12 derivatives by conventional as well as microwave irradiation. These compounds have been characterized on the basis of IR, 1H NMR, MS, and elemental analysis. All the compounds prepared herein were screened for their antibacterial activity. Compounds 4, 5 possess promising antibacterial activity and compound 8 showed significant antibacterial activity.

Synthesis of 5-ethyl-8-oxo-5.8-dihydro-1,3-dioxolo [4,5-g] quinolines and related compounds

Condensation of N-ethyl-3,4-methylenedioxyaniline 1 with diethyl ethoxymethylenemalonate 2 gave the unsaturated ester 3 which on thermal cyclization in refluxing diphenyl oxide gave ester 4. The ester on basic hydrolysis formed free acid 5 which upon treatment with thionyl chloride gave the acid chloride 6. Treatment of 6 with o-phenylenediamine, hydrazine hydrate, ammonia, urea and thiourea gave the amides (7-11). CS2 treatment in presence of KOH on 8 gave 12. 7-12 were prepared by conventional as well as under microwave irradiation. These compounds have been characterized on the basis of elemental analysis, IR, NMR and MS data.

Preparation of 1-(lower alkyl)-1,4-dihydro-7-methyl-4-oxo-1,8-naphthyridine-3-carboxylic acids

A process for producing a compound of the formula: SPC1 Wherein Z is CH or N; R is a lower alkyl group, a lower alkenyl group, a cycloalkyl group or a hydroxyalkyl group; R1 is a hydrogen atom or lower alkyl group; when Z is N, R2, R3 and R4 are a hydrogen atom, a halogen atom a lower alkyl group, a lower alkoxyl group, a lower hydroxyalkyl group, a lower acyloxyalkyl group, trihalogenoalkyl group, a carboxyl group, a cyano group, or an aralkyl group; when Z is CH, R2, R3 and R4 are a hydrogen atom, a halogen atom, a lower alkyl group, a lower alkoxyl group, a trihalogenoalkyl group, a cyano group, a nitro group, an alkylmercapto group, a lower alkylenedioxy group, or a lower alkylene bridge attached to the quinoline nucleus, which comprises heating a compound of the formula SPC2 Wherein R, R1, R2, R3, R4 and Z are as defined above, followed, if desired, by hydrolyzing the product obtained, is disclosed. The product is useful as an antibacterial agent. An intermediate having the formula: SPC3 Wherein A is OR or a halogen atom, and R, R1, R2, R3, R4 and Z are as defined above, and a process for its preparation are also disclosed.