1570075-45-4

Basic information

• Product Name: 4-methoxy-N-phenylpyridin-2-amine
• Synonyms: 4-methoxy-N-phenylpyridin-2-amine
• CAS NO: 1570075-45-4
• Molecular Weight: 200.24
• Mol File: 1570075-45-4.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: 4-methoxy-N-phenylpyridin-2-amine(CAS DataBase Reference)
• NIST Chemistry Reference: 4-methoxy-N-phenylpyridin-2-amine(1570075-45-4)
• EPA Substance Registry System: 4-methoxy-N-phenylpyridin-2-amine(1570075-45-4)

Safety Data

• Hazardous Substances Data: 1570075-45-4(Hazardous Substances Data)

Upstream product

• 89488-29-9 2-bromo-4-methoxypyridine 
• 62-53-3 aniline 
• 108-86-1 bromobenzene 
• 10201-73-7 2-amino-4-methoxypyridine 
• 591-50-4 iodobenzene 

Downstream Products

• 1570075-50-1 N-([1,1'-biphenyl]-2-yl)-4-methoxypyridin-2-amine 
• 578-95-0 10H-acridin-9-one 
• 2835-77-0 (2-aminophenyl)(phenyl)methanone 

Relevant articles and documents

Palladium-Catalyzed Late-Stage ortho-C-H Bond Aroylation of Anilines Using 4-Methoxy-2-pyridinyl as a Removable Directing Group

A synthetic methodology for the late-stage ortho-C-H bond aroylation of anilines with aryl aldehydes led to a variety of ortho-aroylated anilines by the use of palladium(II) acetate, tert-butyl hydroperoxide, and 1,4-dioxane as the catalyst, oxidant, and solvent, respectively, is presented. An N-phenylpyridin-2-amine palladacycle was isolated and characterized by X-ray crystallography. Controlled experiments, radical trapping experiments, and the experiments of the kinetic isotope effect were undertaken to support the proposed reaction mechanism. Syntheses of 2-aminobenzophenone and 9(10H)-acridanone based on the developed methodology were successfully demonstrated.

Palladium(II)-catalyzed direct ortho arylation of 4-methyl-N-phenylpyridin- 2-amines via C-H activation/C-C coupling and synthetic applications

The direct ortho arylation of 4-methyl-N-phenylpyridin-2-amines via palladium(II)-catalyzed C-H activation is described. Treatment of 4-methyl-N-phenylpyridin-2-amine with potassium aryltrifluoroborate using 10 mol % of palladium(II) acetate as the catalyst, 2 equiv of copper(II) acetate as the oxidant, and 1 equiv of p-benzoquinone in tert-butyl alcohol gave ortho-arylated products in modest to excellent yields. This reaction shows good functional group compatibility. A series of 1H NMR titration experiments and controlled experiments elucidating the reaction mechanism were carried out. The key intermediate, 4-methyl-N-phenylpyridin-2-amine palladacycle, was isolated and characterized by X-ray crystallography. The advanced transformations of ortho-phenylated 4-methyl-N-phenylpyridin-2-amine to N-(4-methylpyridin-2-yl)-9H-carbazole, biphenyl-2-amine, and 3-methyl-6-phenylpyrido[1,2-a]benzimidazole were successfully demonstrated as potential synthetic applications.