5414-45-9

Usage

Chemical class

Quinolines, which are heterocyclic organic compounds

Physical state

White solid

Molecular weight

265.77 g/mol

Structural features

Contains a quinoline ring with a 4-chlorophenylmethyl group attached at the 1-position

Form

Exists in a 3,4-dihydro-2H-quinoline form

Pharmaceutical industry

Building block in the synthesis of novel bioactive compounds and potential drug candidates

Industrial applications

Possible uses in materials science or chemical synthesis

InChI:InChI=1/C16H16ClN/c17-15-9-7-13(8-10-15)12-18-11-3-5-14-4-1-2-6-16(14)18/h1-2,4,6-10H,3,5,11-12H2

Upstream product

• 635-46-1 1,2,3,4-tetrahydroisoquinoline 
• 104-83-6 1-Chloro-4-(chloromethyl)benzene 
• 91-63-4 2-methylquinoline 
• 104-88-1 4-chlorobenzaldehyde 
• 1780-19-4 1,2,3,4-tetrahydro-2-methylquinoline 
• 91-22-5 quinoline 

Downstream Products

• 1479311-36-8 N-(4-iodobenzyl)-1,2,3,4-tetrahydroquinaldine 

Relevant academic research and scientific papers

Reductive Alkylation of Quinolines to N-Alkyl Tetrahydroquinolines Catalyzed by Arylboronic Acid

A boronic acid catalyzed one-pot tandem reduction of quinolines to tetrahydroquinolines followed by reductive alkylation by the aldehyde has been demonstrated. This step-economcial synthesis of N-alkyl tetrahydroquinolines has been achieved directly from readily available quinolines, aldehydes, and Hantzsch ester under mild reaction conditions. The mechanistic study demonstrates the unique behavior of organoboron catalysts as both Lewis acids and hydrogen-bond donors.

Hydrogenation of quinaldine and benzylic aldehydes both separately and combined in a tandem hydrogenation-reductive alkylation of quinaldine by aldehydes with iridium benzoquinoline catalysts

A series of cyclometalated benzoquinoline complexes of Ir(III) catalyze the hydrogenation of the heterocyclic ring of quinolines under mild conditions. Our best catalyst is active in a significantly wider range of solvents than our previous systems. In the presence of a suitable base, the Ir(III) species is also able to hydrogenate the C=O bonds of aldehydes. When quinolines and aldehydes are present together, the Ir(III) complex catalyzes a tandem reaction in which the quinoline is first hydrogenated to a tetrahydroquinoline that is subsequently reductively alkylated by the aldehyde. The reductive alkylation competes with the hydrogenation of the aldehyde to the alcohol, and therefore good yields of the alkylated tetrahydroquinoline require the presence of excess aldehyde.