795283-79-3

Basic information

• Product Name: 2-Pyridinecarboxamide,N-[(4-methylphenyl)methyl]-(9CI)
• Synonyms: 2-Pyridinecarboxamide,N-[(4-methylphenyl)methyl]-(9CI)
• CAS NO: 795283-79-3
• Molecular Formula: C₁₄H₁₄N₂O
• Molecular Weight: 226.27376
• Product Categories: METHYL
• Mol File: 795283-79-3.mol
• Article Data: 7

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 2-Pyridinecarboxamide,N-[(4-methylphenyl)methyl]-(9CI)(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Pyridinecarboxamide,N-[(4-methylphenyl)methyl]-(9CI)(795283-79-3)
• EPA Substance Registry System: 2-Pyridinecarboxamide,N-[(4-methylphenyl)methyl]-(9CI)(795283-79-3)

Safety Data

• Hazardous Substances Data: 795283-79-3(Hazardous Substances Data)

Upstream product

• 98-98-6 2-Picolinic acid 
• 104-84-7 para-methylbenzylamine 
• 39901-94-5 2-picolinoyl chloride hydrochloride 

Downstream Products

• 1200444-67-2 C₁₈H₁₈N₂O₅ 
• 1403672-81-0 N-(4-chlorobenzoyl)-N-(4-methylbenzyl)picolinamide 
• 111293-91-5 6-methyl-3-phenylisoquinoline 
• 58083-55-9 6-methylisoindolin-1-one 
• 1300635-93-1 6-methyl-3,4-diphenylisoquinoline 

Relevant articles and documents

Rhodium-Catalyzed Copper-Assisted Intermolecular Domino C?H Annulation of 1,3-Diynes with Picolinamides: Access to Pentacyclic π-Extended Systems

A new mode of reactivity of 1,3-diynes in rhodium-catalyzed oxidative annulation reactions has enabled the rapid assembly of extended π systems from readily available picolinamide derivatives. The process involves a double C?H bond activation and the iterative annulation of two 1,3-diyne units, with each alkyne moiety engaged in an orchestrated insertion sequence with high regiocontrol, leading to the formation of five new C?C bonds and the construction of four fused rings in a single operation. Either isoquinoline-1-carboxamides or fused polycyclic systems can be accessed by a switch in the regioselectivity of the second diyne insertion depending on the reaction conditions. DFT theoretical calculations have elucidated that the cooperative participation of both rhodium and copper in substrate activation, favored in the presence of excess of the copper(II) salt, is key to such a reversal of regioselectivity and subsequent multiple cyclization leading to fused polycyclic products. The role of copper was found to be essential in assisting both multiple insertion and rhodium-walking sequences, with the implication of intermediates with a Rh?Cu bond (2.60 ?).

Tetramethyl Orthosilicate (TMOS) as a Reagent for Direct Amidation of Carboxylic Acids

Tetramethyl orthosilicate (TMOS) is shown to be an effective reagent for direct amidation of aliphatic and aromatic carboxylic acids with amines and anilines. The amide products are obtained in good to quantitative yields in pure form directly after workup without the need for any further purification. A silyl ester as the putative activated intermediate is observed by NMR methods. Amidations on a 1 mol scale are demonstrated with a favorable process mass intensity.

Cobalt-Catalyzed Selective Synthesis of Isoquinolines Using Picolinamide as a Traceless Directing Group

Picolinamide has first been employed as a traceless directing group for the cobalt-catalyzed oxidative annulation of benzylamides with alkynes to synthesize isoquinolines through C-H/N-H bonds activation. Oxygen is used as a terminal oxidant. This protocol exhibits good functional group tolerance and excellent regioselectivity. Both terminal and internal alkynes can be efficiently applied to this catalytic system as substrates.