13466-41-6

Basic information

• Product Name: 2-Hydroxy-4-methylpyridine
• Synonyms: 2-HYDROXY-4-PICOLINE;4-METHYL-2(1H)-PYRIDINONE;4-METHYL-2(1H)-PYRIDONE;4-METHYL-PYRIDIN-2-OL;4-METHYL-2-PYRIDINOL;4-METHYL-2-PYRIDONE;2-HYDROXY-4-METHYLPYRIDINE 97%;2-Hydroxy-4-Piocoline
• CAS NO: 13466-41-6
• Molecular Formula: C₆H₇NO
• Molecular Weight: 109.13
• EINECS: -0
• Product Categories: Pyridine;Pyridine Series;pharmacetical;Pyridines;Heterocycle-Pyridine series
• Mol File: 13466-41-6.mol

Chemical Properties

• Melting Point: 131-134 °C(lit.)
• Boiling Point: 186-187 °C12 mm Hg(lit.)
• Flash Point: 186-187°C/12mm
• Appearance: off-white to light brown crystalline powder
• Density: 1.1143 (rough estimate)
• Refractive Index: 1.5444 (estimate)
• Storage Temp.: Inert atmosphere,Room Temperature
• PKA: pK1:4.529(＋1) (25°C)
• BRN: 107082
• CAS DataBase Reference: 2-Hydroxy-4-methylpyridine(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Hydroxy-4-methylpyridine(13466-41-6)
• EPA Substance Registry System: 2-Hydroxy-4-methylpyridine(13466-41-6)

Safety Data

• Hazard Codes: Xi,Xn
• Statements: 36/37/38-40
• Safety Statements: 26-37/39-36-22
• WGK Germany: 3
• Hazardous Substances Data: 13466-41-6(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
2-Hydroxy-4-methylpyridine is used as a chemical intermediate for the preparation of oxobenzopyrancarboxylate derivatives, which act as inhibitors of serine proteases and human leukocyte elastase. These inhibitors play a vital role in the development of treatments for various diseases and conditions where these enzymes are involved.
Additionally, 2-Hydroxy-4-methylpyridine is used in the synthesis of (indanylamino)(pyridinyloxy)pyrazines and their analogs, which are known as corticotropin-releasing factor type-1 receptor antagonists. These compounds have potential applications in the treatment of stress-related disorders, anxiety, and other conditions related to the dysregulation of the corticotropin-releasing factor system.

Upstream product

• 695-34-1 2-Amino-4-methylpyridine 
• 108-89-4 picoline 
• 100848-70-2 2-methoxy-4-methyl-pyridine 
• 142-08-5 2-Pyridone 
• 74-88-4 methyl iodide 
• 461-87-0 2-fluoro-4-methylpyridine 
• 83766-90-9 4-methyl-2-ethoxypyridine 
• 33245-30-6 4-methyl-2-nitraminopyridine 
• 79917-38-7 4-methyl(2-nitroso)pyridine 
• 108168-80-5 4-methylpyridin-2-yl acetate 
• 4926-28-7 2-Bromo-4-picoline 
• 62022-05-3 4-(tert-butylperoxy)-6-methylpyrimidine 
• 100-42-5 styrene 
• 75-91-2 tert.-butylhydroperoxide 

Downstream Products

• 100848-70-2 2-methoxy-4-methyl-pyridine 
• 179260-78-7 4-methylpyridin-2-yl trifluoromethanesulfonate 
• 3678-62-4 2-chloro-4-picoline 
• 188554-13-4 2-hydroxypyridine-4-carboxaldehyde 
• 89581-53-3 3,5-dibromo-2-hydroxy-4-methylpyridine 
• 164513-38-6 2-hydroxy-5-bromo-4-methylpyridine 
• 18368-59-7 3-bromo-2-hydroxy-4-methylpyridine 
• 1000587-46-1 3-(4-methyl-2-oxo-2H-pyridin-1-yl)-5-nitrobenzoic acid methyl ester 
• 944718-23-4 5-Iodo-4-methyl-pyridin-2-ol 
• 960055-88-3 C₂₂H₂₆N₄O₂ 
• 214479-62-6 6-methyl-3-azabicyclo[4.1.0]heptan-4-one 
• 195819-22-8 2-(2-methoxypyridin-4-yl)ethanol 

Relevant articles and documents

Interplay of method development and mechanistic studies - From aerobic oxidative coupling to radical reactions via alkenyl peroxides

This account summarizes how scientific advances were made in the authors' research group by combining method development in organic synthesis with detailed mechanistic studies. The discovery of an unexpected autoxidative coupling reaction led, by virtue of an ever increased understanding of its mechanism, to a strategy for green C-H functionalization reactions, novel modes of radical generation, addition reactions of ketones to alkenes and new insights into an old reaction, the Baeyer-Villiger oxidation. 1 Introduction 2 Aerobic Oxidative Coupling Reactions with Benzylic C-H Bonds 2.1 The Autoxidative Coupling with Xanthene 2.2 With a Little Help from Light - CHIPS 2.3 Related Autoxidative Coupling Reactions 3 How Does the Autoxidative Coupling Work? 3.1 An Excursion: Formation of Alkenyl Peroxides from Criegee Intermediates in the Atmosphere 3.2 How do Alkenyl Peroxides Form in Solution? Meet Criegee Again 3.3 The Full Mechanism of the Autoxidative Coupling Reaction 4 Previous Indications for Solution Chemistry of Alkenyl Peroxides 4.1 What Might Alkenyl Peroxides be Good for? 5 Concluding Remarks.

Chemoselective Demethylation of Methoxypyridine

A chemoselective demethylation method for various methoxypyridine derivatives has been developed. Treatment of 4-methoxypyridine with L-selectride in THF for 2 h at reflux temperature afforded 4-hydroxypyridine in good yield; no reaction to anisole occurred. The utility of our method was demonstrated by the efficient synthesis of the metabolic substances of the antiulcer agent omeprazole. Chemoselective demethylation at the site of 3,5-dimethyl-4-methoxypyridine in the presence of 4-methoxybenzimidazole was achieved.

Asymmetric Homogeneous Hydrogenation of 2-Pyridones

An asymmetric homogeneous hydrogenation of 2(1H)-pyridones has been developed, using a ruthenium complex bearing two chiral N-heterocyclic carbene (NHC) ligands. To the best of our knowledge, the presented reaction is the first example of a homogeneous asymmetric conversion of 2-pyridones into the corresponding enantioenriched 2-piperidones.

OXAZOLE AND THIAZOLE DERIVATIVES AS SELECTIVE PROTEIN KINASE INHIBITORS (C-KIT)

The present invention relates to compounds of formula I or pharmaceutically acceptable salts thereof: wherein R1, R2, R3, A, Q, W and X are as defined in the description. These compounds selectively modulate, regulate, and/or inhibit signal transduction mediated by certain native and/or mutant proteine kinases implicated in a variety of human and animal diseases such as cell proliferative, metabolic, allergic, and degenerative disorders. More particularly, these compounds are potent and selective native and/or mutant c-kit inhibitors.

PROCESS FOR PRODUCTION OF 2-HYDROXY-4-SUBSTITUTED PYRIDINES

A process for preparing a 2-hydroxy-4-substituted pyridine compound using a microbiological method, a novel microorganism, and a novel compound are provided. According to the process, a function of a microorganism or a product obtained therefrom is exerted on a 4-substituted pyridine of the general formula (1): wherein R is a methyl group, a carboxyl group, a carbamoyl group, a hydroxyiminomethyl group or a cyano group, to obtain the corresponding 2-hydroxy-4-substituted pyridine compound. The novel microorganisms are the Delftia species YGK-A649 (FERM BP-10389), Delftia species YGK-C217 (FERM BP-10388), or Acidovorax species YGK-A854 (FERM BP-10387) and the novel compound is a 2-hydroxy-4-pyridinaldoxime.

Azetidinone compounds useful in the preparation of carbapenem antibiotics and process for preparing carbapenem and penem compounds

Compounds of formula (I): STR1 wherein: R1 is hydrogen or a hydroxy-protecting group; R2 is alkyl, alkoxy, halogen, optionally substituted phenyl or optionally substituted phenoxy; R3 is optionally substituted pyridyl, optionally substituted quinolyl or phenyl group which has a substituent of formula --CYNR5 R6, where Y is oxygen or sulfur, and R5 and R6 are each alkyl, aryl or aralkyl, or R5 and R6 and the nitrogen to which they are attached together form a heterocyclic group; is R4 hydrogen or an amino-protecting group; and Z is sulfur or oxygen; are valuable intermediates in the preparation of carbapenem compounds and retain a desirable configuration during conversion to such carbapenem compounds. Penem and carbapenem compounds having a group of formula --SA' are prepared from a corresponding compound having a substituted thio, sulfinyl or sulfonyl group at this position by reaction with a compound A'SH (where A' is an organic group) in the presence of a salt of a metal of Group II or III of the Periodic Table.

OXYGENATION OF THE UNACTIVATED PYRIDINE SYSTEM BY ACETYL HYPOFLUORITE MADE DIRECTLY FROM F2

Acetyl hypofluorite was found capable of activating the usually unreactive pyridine by substituting the hydrogen at the 2 position by an acetoxy group which then was hydrolyzed to the corresponding pyridinone.Substitutents at 3, 4 or 5 position do not interfere with the reaction, but compounds with substituents at 2 (with the exception of aromatic ones) either do not react or produce tars.The reaction conditions are very mild and the yields are very good for this kind of substitution.Quinolines and pyrazines also react very satisfactorily.

Synthesis of 2-Substituted 4-Pyridylpropionates. Part 2. Alkylation Approach

A synthesis of methyl 3-(2-methoxy-4-pyridyl)propionate (2), a key intermediate in the synthesis of the potent long-acting histamine H2-receptor antagonist SK&F 93574 (1), is described.The key step in the synthesis of compound (1) involves alkylation of 2-methoxy-4-methylpyridine (5) with sodium chloroacetate in the presence of sodamide.The scope and limitations of the alkylation is investigated using a variety of electrophiles.The application of this reaction to other 2-substituted 4-methylpyridines is also discussed.