21683-58-9

Basic information

• Product Name: ethyl 3-(2-methyl-5-pyridyl)-3-oxopropionate
• Synonyms: ethyl 3-(2-methyl-5-pyridyl)-3-oxopropionate;6-Methyl-β-oxo-3-pyridinepropanoic acid ethyl ester;Einecs 244-529-7;Ethyl 3-(6-methylpyridin-3-yl)-3-oxopropanoate
• CAS NO: 21683-58-9
• Molecular Formula: C₁₁H₁₃NO₃
• Molecular Weight: 207.22582
• EINECS: 244-529-7
• Mol File: 21683-58-9.mol
• Article Data: 7

Chemical Properties

• Boiling Point: 310.5°C at 760 mmHg
• Flash Point: 141.6°C
• Appearance: /
• Density: 1.129g/cm³
• Vapor Pressure: 0.000598mmHg at 25°C
• Refractive Index: 1.509
• CAS DataBase Reference: ethyl 3-(2-methyl-5-pyridyl)-3-oxopropionate(CAS DataBase Reference)
• NIST Chemistry Reference: ethyl 3-(2-methyl-5-pyridyl)-3-oxopropionate(21683-58-9)
• EPA Substance Registry System: ethyl 3-(2-methyl-5-pyridyl)-3-oxopropionate(21683-58-9)

Safety Data

• Hazardous Substances Data: 21683-58-9(Hazardous Substances Data)

Usage

General Description

Ethyl 3-(2-methyl-5-pyridyl)-3-oxopropionate is a chemical compound with the molecular formula C12H13NO3. It is a pyridine derivative and belongs to the class of organic compounds known as pyridinecarboxylic acids and derivatives. ethyl 3-(2-methyl-5-pyridyl)-3-oxopropionate is often used as an intermediate in the synthesis of various pharmaceuticals and agrochemicals. It may also have potential applications in the field of organic chemistry as a building block for the preparation of other complex molecules. However, as with any chemical compound, proper handling and safety precautions should be followed when working with ethyl 3-(2-methyl-5-pyridyl)-3-oxopropionate.

InChI:InChI=1/C11H13NO3/c1-3-15-11(14)6-10(13)9-5-4-8(2)12-7-9/h4-5,7H,3,6H2,1-2H3

Upstream product

• 21684-59-3 ethyl 6-methylnicotinate 
• 141-78-6 ethyl acetate 
• 1122-58-3 dmap 
• 5470-70-2 Methyl 6-methylnicotinate 

Downstream Products

• 36357-38-7 1-(6-methyl-pyridin-3-yl)-ethanone 
• 71351-48-9 3-(6-methyl-pyridin-3-yl)-propionic acid ethyl ester 
• 184766-66-3 5-(4-{2-[5-(2-Methyl-[1,3]dioxolan-2-yl)-pyridin-2-yl]-ethoxy}-benzyl)-thiazolidine-2,4-dione 
• 184766-62-9 5-[1-(4-{2-[5-(2-Methyl-[1,3]dioxolan-2-yl)-pyridin-2-yl]-ethoxy}-phenyl)-meth-(Z)-ylidene]-thiazolidine-2,4-dione 
• 184766-39-0 5-(4-(2-(5-(1-(methoxymethoxy)ethyl)pyridin-2-yl)ethoxy)benzyl)thiazolidine-2,4-dione 
• 184766-55-0 4-{2-[5-(2-methyl-1,3-dioxolan-2-yl)-2-pyridyl]ethoxy}benzaldehyde 
• 184766-25-4 4-{2-[5-(1-methoxymethoxy-ethyl)-pyridin-2-yl]-ethoxy}benzaldehyde 
• 184766-50-5 2-[5-(2-methyl-1,3-dioxolan-2-yl)-2-pyridyl]ethanol 
• 184766-45-8 3-(2-methyl-1,3-dioxolan-2-yl)-6-methylpyridine 
• 146062-45-5 Ketopioglitazone 
• 146062-44-4 Hydroxypioglitazone 
• 146062-57-9 3-(1-(methoxymethoxy)ethyl)-6-methylpyridine 
• 56019-64-8 5-(1-hydroxyethyl)-2-methylpyridine 

Relevant articles and documents

PHARMACEUTICAL COMPOUNDS

Benzodiazepine derivatives of formula (I): (I) wherein: each of R1 and R2 is independently H or halo; either (i) T is N, Z is C, ---a--- and ---c--- are bonds, and ---b--- and ---d--- are absent; or (ii) T is C, Z is N, ---b--- and ---d--- are bonds, and ---a--- and ---c--- are absent; each of R3 and R4 is independently halo, -OR6, -NR6R7, -COR8, -C(O)OR8, -CON(R8)2 or -R6; R5 is H or halo; each of R6 and R7 is independently H or a group selected from C1-C6 alkyl, C3-C10 cycloalkyl, C6-C10 aryl, 4- to 10-membered heterocyclyl and 4- to 10-membered heteroaryl, the group being unsubstituted or substituted; R8 is H or C1-C6 alkyl, each R8 being the same or different when two are present; n is 0 or 1; and one of V, W, X and Y is N or CH and the other three are CH; and the pharmaceutically acceptable salts thereof are inhibitors of RSV and can therefore be used to treat or prevent an RSV infection.

Efficient one-pot selective reduction of esters in β-ketoesters using LiHMDS and lithium aluminium hydride

The ester functionality in β-keto esters is selectively reduced in one-pot, first by enolization using LiHMDS and then reduced with lithium aluminium hydride. This method produces β-hydroxyl ketones from the corresponding β-keto esters in high yield.

Synthesis and biological activity of metabolites of the antidiabetic, antihyperglycemic agent pioglitazone

Pioglitazone (5-(4-(2-(5-ethyl-2-pyridyl)ethoxy)benzyl)-2,4- thiazolidinedione, 2) is a prototypical antidiabetic thiazolidinedione that had been evaluated for possible clinical development. Metabolites 6-9 have been identified after dosing of rats and dogs. Ketone 10 has not yet been identified as a metabolite but has been added to the list as a putative metabolite by analogy to alcohol 6 and ketone 7. We have developed improved syntheses of pioglitazone (2) metabolites 6-9 and the putative metabolite ketone 10. These entities have been compared in the KKA(y) mouse model of human type-II diabetes to pioglitazone (2). Ketone 10 has proven to be the most potent of these thiazolidinediones in this in vivo assay. When 6-10 were compared in vitro in the 3T3-L1 cell line to 2, for their ability to augment insulin-stimulated lipogenesis, 10 was again the most potent compound with 6, 7, and 9 roughly equivalent to 2. These data suggest that metabolites 6, 7, and 9 are likely to contribute to the pharmacological activity of pioglitazone (2), as had been previously reported for ciglitazone (1).