[58986-28-0] C5H7NaO3 (MW 138.11) InChI = 1S/C5H8O3.Na/c1-2-8-5(7)3-4-6;/h3-4,6H,2H2,1H3;/q;+1/p-1/b4-3-; InChIKey = ITWVTNYFGKFDGE-LNKPDPKZSA-M (a three-carbon β-dicarbonyl building block) Alternate Names: ethyl formylacetate, sodium salt. Solubility: sol H2O and protic solvent; insol THF. Preparative Methods: the material is usually prepared by the condensation of ethyl acetate and ethyl formate in the presence of a strong base such as Sodium Hydride, sodium alkoxide, or Sodium metal (eq 1).2-6 (1) The condensation is accompanied by side reactions, and the white solid obtained is generally about 70% pure. Preparation under carbon monoxide pressure has been suggested to improve the yield and purity.6 The compound has also been prepared by the careful hydrolysis of ethyl β-chloroacrylate.7 The free acid (malonic semialdehyde) is easily oxidized in air,1 and the various parent esters8-10 are all subject to polymerization, although the t-butyl ester can be stored at −80 °C without deterioration for a month.10a Handling, Storage, and Precautions: salts and free acid have limited stability1 and should be prepared as needed; use in a fume hood.

5-fluoro-3-[3-[4-(5-methoxy-4-pyrimidinyl)-1-piperazinyl]-propyl]-1H-indole dihydrochloride (1) facilitates 5-HT neurotransmission and was an antidepressant drug candidate. The development of a safe, rugged process for the large-scale, chromatography-free preparation of this compound is described, The main areas of optimization included a Fischer indole synthesis, preparation and chlorination of a monohydroxypyrimidine, and coupling of the resultant fragments to prepare the drug substance.

Two new and improved syntheses of the antiarrhythmic drug Encainide, 1, are presented. The first approach is based on the condensation of 2-picolyllithium with the p-anisoyl amide of methyl anthranilate, 3, followed by a series of catalytic hydrogenations and methylation. The second route relies on a particularly facile condensation reaction between N-methylpicolinium methyl sulfate and o-nitrobenzaldehyde to produce the alcohol 17c in high yield which is converted to the olefin 18c by a novel dehydration procedure and then to the final molecule, by catalytic hydrogenation over platinum followed by acylation.

AbstractThe synthesis of 3,4‐dihydro‐4‐oxothieno[2,3‐d]pyrimidine‐2‐carboxylates via acid catalyzed reactions of various 2‐aminothiophene‐3‐carboxylates with activated nitriles is presented. The requisite thiophenes were prepared regioselectively by methods which represent improvements over previously published procedures.

AbstractThe synthesis and x‐ray crystal structure of BMY 13754, a 1,2,4‐triazolin‐3‐one under clinical evaluation as an antidepressant agent, is described. Several synthetic strategies are discussed.

ADVERTISEMENT RETURN TO ISSUEPREVArticleNEXTCyclization of 2'-formamido-4',5'-dimethoxypropiophenone with ammoniaGary D. MaddingCite this: J. Org. Chem. 1972, 37, 11, 1853–1854Publication Date (Print):June 1, 1972Publication History Published online1 May 2002Published inissue 1 June 1972https://pubs.acs.org/doi/10.1021/jo00976a052https://doi.org/10.1021/jo00976a052research-articleACS PublicationsRequest reuse permissionsArticle Views36Altmetric-Citations4LEARN ABOUT THESE METRICSArticle Views are the COUNTER-compliant sum of full text article downloads since November 2008 (both PDF and HTML) across all institutions and individuals. These metrics are regularly updated to reflect usage leading up to the last few days.Citations are the number of other articles citing this article, calculated by Crossref and updated daily. Find more information about Crossref citation counts.The Altmetric Attention Score is a quantitative measure of the attention that a research article has received online. Clicking on the donut icon will load a page at altmetric.com with additional details about the score and the social media presence for the given article. Find more information on the Altmetric Attention Score and how the score is calculated. Share Add toView InAdd Full Text with ReferenceAdd Description ExportRISCitationCitation and abstractCitation and referencesMore Options Share onFacebookTwitterWechatLinked InRedditEmail Other access optionsGet e-Alertsclose Get e-Alerts