80356-43-0

Upstream product

• 1873-60-5 3-ethyl-4-hydroxyquinolin-2(1H)-one 
• 3287-99-8 benzylamine hydrochloride 
• 1885-29-6 anthranilic acid nitrile 
• 88629-04-3 N-(α-bromobutyryl)-2-cyanoanilide 
• 80356-45-2 4-Benzylamino-3-ethyl-1H-quinolin-2-one 

Downstream Products

• 110216-99-4 3-Ethyl-4-tosyloxy-2(1H)-chinolon 
• 1873-60-5 3-ethyl-4-hydroxyquinolin-2(1H)-one 

Relevant academic research and scientific papers

Methods for the Synthesis of 4-Azido-2(1H)-quinolones

4-Hydroxy-2-quinolones 1 are generally found to be converted to the 4-azidocompounds 3 via the 4-chloroquinolones 2, the 4-tosyloxyquinolones 6, or the 4-aminoquinolones 4, respectively.Choice of the reaction conditions and yields depend on the substituen

A NEW SYNTHESIS OF 4-AMINO-2-QUINOLINONES

Addition of Grignard or organolithium reagents to N-(α-haloacyl)-N-alkylsubstituted anthranilonitriles (e.g.N-(2-bromopropionyl)-N-methyl-2-cyanoaniline)induced anion formation followed by cyclization to 4-amino-2-quinolinones (e.g. 4-amino-1,3-dimethyl-2-quinolinone (10)).Substrates lacking α-hydrogen atoms, such as N-α-bromoisobutyryl)-2-cyanoaniline, also yielded 3,3-dimethylquinolinedione (9b) by cyclization.In these cases the initial step is a halogen-metal exchange reaction.