32953-23-4

Basic information

• Product Name: diethyl [[N-ethyl-3,4-(methylenedioxy)anilino]methylene]malonate
• Synonyms: diethyl [[N-ethyl-3,4-(methylenedioxy)anilino]methylene]malonate;[[(1,3-Benzodioxol-5-yl)(ethyl)amino]methylene]propanedioic acid diethyl ester;2-[[1,3-Benzodioxol-5-yl(ethyl)amino]methylene]malonic acid diethyl ester;2-[[N-Ethyl-3,4-(methylenedioxy)anilino]methylene]malonic acid diethyl ester
• CAS NO: 32953-23-4
• Molecular Formula: C₁₇H₂₁NO₆
• Molecular Weight: 335.35174
• EINECS: 251-303-1
• Mol File: 32953-23-4.mol
• Article Data: 4

Chemical Properties

• Boiling Point: 418.2°Cat760mmHg
• Flash Point: 206.7°C
• Appearance: /
• Density: 1.237g/cm³
• Vapor Pressure: 3.34E-07mmHg at 25°C
• Refractive Index: 1.556
• PKA: 0.08±0.70(Predicted)
• CAS DataBase Reference: diethyl [[N-ethyl-3,4-(methylenedioxy)anilino]methylene]malonate(CAS DataBase Reference)
• NIST Chemistry Reference: diethyl [[N-ethyl-3,4-(methylenedioxy)anilino]methylene]malonate(32953-23-4)
• EPA Substance Registry System: diethyl [[N-ethyl-3,4-(methylenedioxy)anilino]methylene]malonate(32953-23-4)

Safety Data

• Hazardous Substances Data: 32953-23-4(Hazardous Substances Data)

Usage

InChI:InChI=1/C17H21NO6/c1-4-18(12-7-8-14-15(9-12)24-11-23-14)10-13(16(19)21-5-2)17(20)22-6-3/h7-10H,4-6,11H2,1-3H3

Upstream product

• 87-13-8 diethyl 2-ethoxymethylenemalonate 
• 32953-14-3 N-ethyl-3,4-(methylenedioxy)aniline 
• 18856-68-3 diethyl N,N-dimethylaminomethylenemalonate 
• 6296-99-7 diethyl aminomethylenemalonate 
• 114954-61-9 ethyl 4-aza-5-dimethylamino-2-ethoxycarbonyl-2,4-pentadienoate 

Downstream Products

• 19658-59-4 5-ethyl-8-oxo-5,8-dihydro-[1,3]-dioxolo[4,5-g]quinoline-7-carbonyl chloride 
• 16172-03-5 ethyl 5-ethyl-5,8-dihydro-8-oxo-1,3-dioxolo<4,5-g>quinoline-7-carboxylate 
• 14698-29-4 oxolinic Acid 
• 26893-17-4 ethyl 8-chloro-[1,3]dioxolo[4,5-g]quinoline-7- carboxylate 

Relevant articles and documents

Synthetic method of oxolinic acid

The invention relates to a synthetic method of oxolinic acid, and belongs to the technical field of chemical synthesis. The synthetic method provided by the invention includes the following steps: (1)reacting a compound I with a compound II at 120-150 DEG C to obtain a compound III; (2) cooling a mixed solution obtained in the step (1) to 70-110 DEG C, adding acetic anhydride and concentrated sulfuric acid in order, and heating to 120-140 DEG C for reaction; and (3) after the reaction in the step (2) is finished, lowering the temperature to 80-95 DEG C, and adding water for a hydrolysis reaction to obtain the oxolinic acid. The method of the invention is high in yield, greatly reduced in production cost and good in product quality, and is suitable for industrial production. The concrete synthetic route is shown in the description.

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.