794563-59-0

Basic information

• Product Name: N-(5-chloro-2-methylphenyl)picolinamide
• Synonyms: N-(5-chloro-2-methylphenyl)picolinamide
• CAS NO: 794563-59-0
• Molecular Weight: 246.696
• Mol File: 794563-59-0.mol
• Article Data: 4

Chemical Properties

• CAS DataBase Reference: N-(5-chloro-2-methylphenyl)picolinamide(CAS DataBase Reference)
• NIST Chemistry Reference: N-(5-chloro-2-methylphenyl)picolinamide(794563-59-0)
• EPA Substance Registry System: N-(5-chloro-2-methylphenyl)picolinamide(794563-59-0)

Safety Data

• Hazardous Substances Data: 794563-59-0(Hazardous Substances Data)

Upstream product

• 98-98-6 2-Picolinic acid 
• 95-79-4 5-chloro-2-methyl-benzenamine 

Downstream Products

• 1575753-89-7 C₁₇H₁₈ClN₃O₂ 
• 1621481-56-8 {4-chloro-2-[(pyridine-2-carbonyl)amino]phenyl}methyl acetate 

Relevant articles and documents

Directed C-H Functionalization Reactions with a Picolinamide Directing Group: Ni-Catalyzed Cleavage and Byproduct Recycling

An efficient strategy for the cleavage of the picolinamide directing group (DG) and recycling of the byproduct generated has been developed. In this protocol, picolinamides were first Boc activated into tertiary N-Boc-N-substituted picolinamides. These were then cleaved via a Ni-catalyzed esterification reaction with EtOH to give valuable N-Boc protected amines. Ni(cod)2 was used as a catalyst without any ligands or base additives. The byproduct, ethyl 2-picolinate can be used to install the picolinamide DG in a direct or indirect manner on amines. The protocol exhibits a broad functional group tolerance and high yields. To demonstrate the utility of this approach, it was applied on many selected examples from the recent C-H functionalization literature featuring 2-picolinamide as a DG.

Palladium-catalyzed picolinamide-directed acetoxylation of unactivated γ-C(sp3)-H bonds of alkylamines

We report a new protocol for palladium-catalyzed acetoxylation of the γ-C(sp3)-H bonds of N-alkylpicolinamide substrates using PhI(OAc)2 oxidant. These reactions involve the use of substoichiometric amounts of Li2CO3 additive, which effectively suppresses the competing intramolecular C-H amination process. Under these conditions, N-propylpicolinamides bearing α substituents can be cleanly converted to γ-acetoxylated amine products in excellent yield. This C-H acetoxylation can also be used in concert with other Pd-catalyzed picolinamide-directed C-H functionalization reactions for rapid scaffold diversification.