35022-83-4

Basic information

• Product Name: 1(2H)-Pyridinecarboxylic acid, 2-phenyl-, ethyl ester
• CAS NO: 35022-83-4
• Molecular Formula: C14H15NO2
• Molecular Weight: 229.279
• Mol File: 35022-83-4.mol

Chemical Properties

• CAS DataBase Reference: 1(2H)-Pyridinecarboxylic acid, 2-phenyl-, ethyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: 1(2H)-Pyridinecarboxylic acid, 2-phenyl-, ethyl ester(35022-83-4)
• EPA Substance Registry System: 1(2H)-Pyridinecarboxylic acid, 2-phenyl-, ethyl ester(35022-83-4)

Safety Data

• Hazardous Substances Data: 35022-83-4(Hazardous Substances Data)

Upstream product

• 110-86-1 pyridine 
• 100-59-4 phenylmagnesium chloride 
• 541-41-3 chloroformic acid ethyl ester 
• 63755-30-6 N-ethoxycarbonylpyridinium chloride 

Relevant articles and documents

REGIOSELECTIVE SYNTHESIS OF 4-ALKYLPYRIDINES VIA 1,4-DIHYDROPYRIDINE DERIVATIVES FROM PYRIDINE

N-Ethoxycarbonylpyridinium chloride (1) reacted with at 4-position with almost complete regioselectivity (better than 99percent) to afford the corresponding 1,4-dihydropyridine derivatives (2) in high yields (81 ca. 94percent).The dihydropyridines were readily oxidized by oxygen to give 4-alkylpyridines (4:38 ca. 68percent yields).

A Convenient Method for the Regioselective Synthesis of 4-Alkyl(aryl)pyridines Using Pyridinium Salts

RCu.BF3 reacted with 1-ethocycarbonylpyridinium chloride at the 4-position with almost complete regioselectivity (>99percent) to afford the corresponding 1,4-dihydropyridine derivatives in high yields (81-94percent).The dihydropyridines were oxidized by oxygen to give 4-alkyl(aryl)pyridines (38-68percent).Grignard reagents also reacted with 1-t-butyldimethylsilylpyridinium triflate with almost complete regioselectivity (>99percent) to afford the corresponding 1,4-dihydropyridines, which were easily oxidized to give 4-substituted pyridines in higher yields than above (58-70percent).

Regioselective Addition of Grignard Reagents to 1-Acylpyridinium Salts. A Convenient Method for the Synthesis of 4-Alkyl(aryl)pyridines

The addition of Grignard reagents to 1-acylpyridinium salts afforded 1-acyl-2-alkyl(aryl)-1,2-dihydropyridines and 1-acyl-4-alkyl(aryl)-1,4-dihydropyridines.The regioselectivity of this reaction, 1,2- vs. 1,4-addition, was examined and found to be dependent upon the structures of the Grignard reagent and the 1-acyl group.Pyridine, 2-picoline, and 3-picoline were studied, and in most cases, significant amounts of 1,4-addition occurred.When a catalytic amount of cuprous iodide was present, nearly exclusive 1,4-addition resulted.The crude 1,4-dihydropyridines were aromatized by heating with sulfur to provide 4-substituted pyridines and picolines in good yield and high isomeric purity.