Ethyl 2-pyridylacetate

Ethyl 2-pyridylacetate + diethyl ethoxymethylenemalonate 6 hr at 160° without removal 59-63 of alcohol formed 27... 

Ethyl 2-pyridylacetate + ethyl ethoxymethylenenitroacetate 10 min at 60°, 20 min at 100° without removal of alcohol formed 48 27... 

Ethyl 2-pyridylacetate + ethyl ethoxymethyleneacetoacetate NaOEt (catalytic amount) in benzene, 15 hr at 30° 70 27... 

Ethyl 2-pyridylacetate + ethyl ethoxymethylenecyanoacetate Na in anhydrous EtgO, stirred 7 hr at 25° 20 26a... 

Ethyl n-propylmalonate, 486 Ethyl n-propyl ketone, 340 4-Ethylpyridine, 844 Ethyl 2-pyridylacetate, 931, 932 Ethyl salicylate, 783 Ethyl sulphite, 304 Ethyl -valerate, 382, 389 Ethyl vinylacetate, 382, 389 Ethylenediamine-adipic acid polymer, 1019,1025 Ethylene glycol, 285 Ethylene glycol, monoalkyl ethers of, 170, 444... 

Using an a-bromo ester instead of an a-bromo ketone the 2-hydroxyindolizine (111) has been obtained from ethyl 2-pyridylacetate (63JCS3277, 80JOC5100). By variation of R1 in (106), 1-cyano-, 1-amino-, 1-hydroxy- and 1-nitro-indolizines have been obtained. 

Thyagarajan and Gopalakrishnan utilized the reaction of ethyl 2-pyridylacetate with reagents of the type 69, where R = COOEt, N02, or COCH3 to synthesize quinolizones of the general structure 70.81,83 When they extended the reaction to some 2,6-lutidylketones (71), they found that, whereas quinolizones were formed when R = COOEt, an... 

The reaction of ethyl bromopyruvate with ethyl 2-pyridylacetate, originally thought84 to yield a quinolizine, has been shown by Bragg and Wibberley12,65 and by Kappe86 to give the indolizine (73). 

Methyl 2-pyridylacetate in ether with MP yields a mixture of 106, 107, and 108 which could be formed through a zwitterion corresponding to 95,296 and 109. The 1-propanoyl derivative of 109 is obtained from l-(2-pyridyl)butan-2-one. However, ethyl 2-pyridylacetate with phenyl-propiolic esters apparently gave only 110, and, if sodium methoxide was... 

The complex bis(pentane-2,4-dionato)-jLi,/i. -dimethoxy-dicopper(II) has been found to be a very effective and selective catalyst for ester exchange of both 2-ethoxycarbonylpyridine and ethyl 2-pyridylacetate to give the corresponding methyl esters.491... 

Activation of alkyl substituents is illustrated by the synthesis of the isomeric pentylpyridines (Expt 8.33) and ethyl 2-pyridylacetate (Expt 8.32, cognate preparation). Thus removal of a proton from the 2-methyl group of 2-methyl-pyridine (2-picoline) with the aid of base (e.g. sodamide) gives a mesomerically... 

Ethyl 2-pyridylacetate has been converted into l-carbethoxy-3-nitro-4H-quinolizin-4-one (102) by condensation with ethyl /J-ethoxy-a-nitroacrylate [Eq. (33)].94... 

Ethyl 2-pyridylacetate reacts with diethyl ethoxymethylene malonate to give cyclic compound 64, which, on refluxing in hydrochloric acid, affords 4-quinolizone (65) (51JA3681). The 40% contribution of the betaine form 66 to the resonance hybrid was estimated on the basis of the H-NMR spectrum of 65 (73JOC4391). 

Mannich reaction of [Cu(en)2]2+ with methanal and ethyl-2-pyridylacetate forms the 6,13-bis (2-pyridyl)-cyclam compound in 6% yield as trans- and m-isomers in 9 1 mole ratio.96 (see also Section 1.20.6.2)... 

Addition of ethyl 2-pyridylacetate to diethyl vinylphosphonate without solvent using EtONa as catalyst produces diethyl 3-(ethoxycarbonyl)-3-(2-pyridyl)propylphosphonate in 60% yield. Acid hydrolysis with 10 M HCl followed by decarboxylation of the product gives the 3-(2-pyridyl)propylphosphonic acid in 50% yield (Scheme 8.60). 

Ethyl phenylacetylmalohate, 25, 73 Ethyl i8-phenyl-(3-hydroxypropio-NATE, 21, 51 Ethyl propionate, 21, 43 Ethyl propylcyanoacetate, 26, 33 4-Ethylpyridine, 27, 38 Ethyl 2-pyridylacetate, 29, 44 1-Ethylpyrrolidine, 25, 19 Ethyl succinate, 26, 42 Ethyl thiourea, 21, 84... 

Oxysparteine was also the intermediate which furnished conclusive proof of the ring structure of all the Cw lupin alkaloids. Clemo, Morgan, and Raper in 1936 (260) announced the synthesis, from non-alkaloid starting materials, of a compound with structure XCV and established the identity of this compound with the d/-oxysparteine obtained by alkaline ferricyanide oxidation of dZ-sparteine. The s3Tithesis of dZ-oxy-sparteine (XCV) was accomplished as outlined below. The Claisen condensation of ethyl 2-pyridylacetate (XCVI) with ethyl orthoformate... 

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