81763-96-4

Upstream product

• 16576-25-3 2-benzoylquinoline 
• 2739-16-4 3,4-dihydro-2H-quinoline-1-carbaldehyde 
• 635-46-1 1,2,3,4-tetrahydroisoquinoline 
• 121565-21-7 1,2,3,4-tetrahydroquinolin-1-carboxylic acid lithium salt 
• 100-52-7 benzaldehyde 
• 81763-92-0 tert-butyl(3,4-dihydro-2H-quinolin-1-ylmethylene)amine 

Relevant academic research and scientific papers

Partial hydrogenation of substituted pyridines and quinolines: A crucial role of the reaction conditions

Hydrogenation of pyridyl and quinolyl compounds 2-substituted with a carbonyl group (1a-c and 2b,c) using PtO2 and 1 equiv. of HCl (conditions A) provides clean and total formation of the desired amino alcohol (hydrogenation of the heterocyclic ring and of the carbonyl) while under conditions B1 and/or B2 (concentrated HCl or pure CF 3CO2H) the heterocyclic ring remains untouched and other aromatic parts are hydrogenated providing complex mixtures. When the heterocyclic ring is substituted by an alkyl group (quinaldine 3) conditions A provide mixtures while under conditions B2 (pure CF 3CO2H) the benzene ring is cleanly hydrogenated leading to a pure product.

α-Metallation of Tetrahydroquinoline and Indoline via their Lithium Carbamates: A Versatile One-Pot Procedure

1,2,3,4-Tetrahydroquinoline and indoline as their lithium carbamates undergo α-metallation with a ButLi-KOBut mixture.The resulting α-metallo species react with carbonyl electrophiles to give the α-alkylated secondary amines in an overall one-pot procedure.

DIPOLE STABILIZED α-AMINO-CARBANIONS. III. METALATION-ALKYLATION OF INDOLINES, TETRAHYDROQUINOLINES AND N-METHYLANILINES.

Metalation of the 2-position in indolines and tetrahydroquinolines is feasible via their formamidine derivatives using tert-butyllithium.The N-methyl group in N-methylanilines is also metalated using this base.