Ethyl 4-ethoxybenzoate

This with potassium hydroxide in methanol forms de-OiV-dimethylarmepavine, m.p. 86-7°, (B. HCl, m.p. 229-30°) of which the methiodide, m.p. 233-4°, on treatment with alkali decomposes into trimetHylamine and a -p-anisyl-/3-(3 4-dimethoxy- 6 - vinylphenyl) -ethylene, m.p. 79°. The latter is oxidised by permanganate in acetone to anisic and m-hemipinic acids. With ethyl sulphate and alkali, armepavine gives 0-ethylarmepavine, an oil, which permanganate oxidises to p-ethoxybenzoic acid. Armepavine is similarly oxidised to p-hydroxybenzoic acid and l-keto-6 7-dimethoxy-2-methyl-1 2 3 4-tetiahydrowoquinoline and is therefore 6 7-dimethoxy-l-p-hydroxybenzyI-2-methyI-l 2 3 4-tetrahydrowoquinoline, i.e., it is laudanosine (p. 187) with MeO. at C replaced by H and MeO at C changed to HO. ... 

RN 94-23-5 MF C15H23NO3 MW 265.35 CN 4-ethoxybenzoic acid 2-(diethylamino)ethyl ester... 

Ethylenimine, 30, 38 toxic properties of, 30, 40 Ethyl o-ethoxybenzoate, 32, 75 Ethyl formate, 32, 32 Ethyl glycidyl ether, 31, 3 2-Ethylhexanaldoxime, 32, 67 2-Ethylhexanamide, 32, 65 2-Ethylhexanoic acid, 32, 66 2-Ethylhexanonitrile, 32, 65 Ethylidene bromide, 32, 55 Ethyl iodide, 31, 34 Ethyl isodehydroacetate, 32, 76 Ethyl lactate, 31, 59, 60 5-ETHYL-2-METHYLPYRIDINE, 30, 41 Ethyl orthocarbonate, 32, 68 Ethyl orthoformate, 32, 5 Ethyl orthosilicate, 32, 5 Ethyl phenylazoacetoacetate, 32, 85 Ethyl phenylcyanoacetate, 30,43,80 Ethyl 0-phenyl-/3-cyanopropionate, 30, 84... 

Other methods of preparing flavone include the action of ethanolic alkali on 2 -acetoxy-a,/3-dibromochalcone 7 Claisen condensation of ethyl o-ethoxybenzoate and acetophenone, and cyclization of the resulting 1,3-diketone with hydriodic acid 8 and treatment of 3-bromoflavanone with potassium hydroxide in ethanol.9 Flavone has also been prepared from ethyl phenyl-propiolate by condensation with sodium phenoxide and subsequent cyclization with phosphorus pentachloride in benzene 10 by fusing o-hydroxyacetophenone with benzoic anhydride and sodium benzoate 11 by the dehydrogenation of 2 -hydroxychal-cone with selenium dioxide 12 and by the action of alkali on flavylium chloride.13... 

Ethylene glycol 39, 13 drying of, 37, 42 monomethyl ether, 32, 43 Ethylenesulfonyl chloride, 2-PHENYL-, 34, 85 Ethylenmine, 30, 38 toxic properties of, 30, 40 Ethyl o-ethoxybenzoate, 32, 75 Ethyl ethoxymethylenecj anoacetate, 39, 34... 

This gradation is illustrated by the results obtained with the diazonium salts from the isomeric aminobenzoic adds. When the orthQ diazonium nitrate is treated with absolute ethanol only reduction occurs 23 ethyl benzoate is obtained in 63% yield.f The diazonium add sulfate derived from ra-aminobenzoic add is converted into a mixture of ethyl benzoate and ethyl m-ethoxybenzoate, the former preponderating.24 23122 Finally, with the p-diazonium salts the ether reaction is the favored one 22123 from the nitrate the yields of p-ethoxy benzoic add and ethyl benzoate are 60% and 12%, respectively. 

In addition to 4-hydroxydihydrocinnamic acid, spermine is formed in the acid-catalyzed hydrolysis of 173 (2 iV HC1,150°C, sealed tube). The expected 4-methoxycinnamic acid has not been found. If the phenolic hydroxyl group in 173 is ethylated and the product oxidized with KMn04, 4-meth-oxy- and 4-ethoxybenzoic acid are the products and they must have been formed from the differently substituted benzene rings in 173 (see Scheme 31). 

SYNS 4-ACETAMIDO-2-ETHOLXBENZOIC ACID METHYL ESTER 2-ETHOXY-4-ACETAMIDOBENZOID ACID METHYL ESTER ETHYL PABATE METHYL 4-ACETAMIDO-2-ETHOXYBENZOATE... 

A few polysubstituted benzenes have been evaluated for their possible use in protozoal chemotherapy. RC-12 (57) is a pyrocatechol derivative, which was initially found to possess promising antimalarial activity. However, in clinical trials against P. vivax it failed to protect volunteers exposed to infected mosquitoes [16]. Another compound ethyl 4-acetamido-2-ethoxybenzoate (ethopabate, 58) has been found to exhibit anticoccidial activity [45,57]. Also some nitrobenzamides have been shown to have anticoccidial properties. The important drugs of this class are zoalene (59) [58], nitromide (60) [59] and alkomide (61) [45,60]. The detailed SAR on nitrobenzamides has been studied [59,61]. 

Ethopabate 4-A ceta mido 2 th0xy ben zoic add methyl ester merhy] 4-acetamido-2-ethoxybenzoate 2-ethoxy -4 acetamidobenzoic acid methyl ester ethyl pabate, Ci2H.,N04 mol wt 237,25. C 60.75%, H 6.37% N 5,90%, O 26.98%. Prepn Grim me, Schmitz Ber, 87, 179 (1954) ... 

Pseudocodamine (LIV) was found to be l-(3-methoxy-4-hydroxybenzyl)-2 - methyl -6,7- dimethoxy -1,2,3,4-tetrahydroisoquinoline. Ethylation with diazoethane led to an ethyl ether (m.p. 176-180°) which could be oxidized to A -methylcorydaldine and 3-methoxy-4-ethoxybenzoic acid (LXXIV). 

Fig. 13 Profiles of temperature rising elution fractionation of PP produced by catalysts with different internal and external donors (reproduced from [59]). DIBP disobutylphthalate, TFPMDMS 3,3,3-trifiuoropropyl(methyl)dimethoxysilane, CHMDMS cyclohexyl(methyl)dimethoxysilane, EB ethylbenzoate, PEEB ethyl p-ethoxybenzoate, DCPDMS dicyclopentyldimethoxysilane. The deviation in the peak positions indicates that the isospecificity of the main active sites varies according to the combination of donors...

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