845960-45-4

Upstream product

• 110-89-4 piperidine 
• 845960-43-2 6-chloro-4-(4-ethoxyphenyl)-1-phenylpyridin-2(1H)-one 
• 67141-88-2 β-(4-ethoxyphenyl)glutaconic acid 
• 946494-15-1 4-(4-ethoxy-phenyl)-1-phenyl-3H-pyridine-2,6-dione 
• 103-73-1 Phenetole 

Relevant academic research and scientific papers

Synthesis of novel 6-substituted-aminopyridin-2(H)-ones

6-Substituted-amino-4-(4-ethoxyphenyl)-1-phenylpyridin-2(H)-ones 4,5 have been prepared from citric acid. It is treated with conc. H2SO 4 and then with phenetole to give β-arylglutaconic acid which on fusion with arylamine results in 4-(4-ethoxyphenyl)-1-aryl-5-H-pyridine-2,6- diones 2. When 2 (Ar=phenyl) is reacted with phosphorous oxychloride it gives 6-chloro-4-(4-ethoxyphenyl)-1-phenylpyridin-2(H)-one 3, which on treatment with secondary amines yields 6-substituted-amino-4-(4-ethoxyphenyl)-1-phenylpyridin- 2(H)-ones 4 and 5. When 4 and 5 are subjected to azo coupling with different aryldiazonium chlorides furnish two isomers 6-substituted-amino-4-(4- ethoxyphenyl)-1-phenyl-3-(arylazo)pyridin-2(H)-ones 6a-j and 7a-j and 6-substituted-amino-4-(4-ethoxyphenyl)-1-phenyl-5-(arylazo)pyridin-2(H)-ones 6k-t and 7k-t. However, the Mannich reaction on 4 and 5 gives only single product identified as 6-substituted-amino-4-(4-ethoxyphenyl)-1-phenyl-3- (aminomethyl)pyridin-2(H)-ones 8a-b and 9a-b. All the compounds have been characterized by elemental analysis, IR and NMR spectral data.