157027-28-6

Basic information

• Product Name: 3-benzyl-2,4-dichloroquinoline
• Synonyms: 3-benzyl-2,4-dichloroquinoline
• CAS NO: 157027-28-6
• Molecular Weight: 288.176
• Mol File: 157027-28-6.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: 3-benzyl-2,4-dichloroquinoline(CAS DataBase Reference)
• NIST Chemistry Reference: 3-benzyl-2,4-dichloroquinoline(157027-28-6)
• EPA Substance Registry System: 3-benzyl-2,4-dichloroquinoline(157027-28-6)

Safety Data

• Hazardous Substances Data: 157027-28-6(Hazardous Substances Data)

Upstream product

• 607-81-8 diethyl 2-benzylmalonate 
• 146764-88-7 3-benzyl-1H-quinoline-2,4-dione 
• 15000-41-6 3-benzyl-4-hydroxy-2-quinolone 

Downstream Products

• 157027-52-6 C₃₄H₂₆ClN₂P 
• 110216-88-1 4-amino-3-benzyl-2(1H)-quinolone 
• 157027-35-5 4-Azido-3-benzyl-2-chloro-quinoline 

Relevant articles and documents

Reaction of some 2-quinolone derivatives with phosphoryl chloride: Synthesis of novel phosphoric acid esters of 4-hydroxy-2-quinolone

3-Chloroquinoline-2,4-diones do not react with phosphoryl chloride, however, 2,4-dichloroquinolines and/or 4-chloroquinolin-2-ones are formed in the presence of N,N-dimethylaniline. Along with these compounds, small quantities of novel dihydrogen phosphates of 4-hydroxyquinolin-2-ones were isolated. We outline a simple procedure that allows for the preparation of these compounds in moderate to good yields. All compounds were characterized by 1H and 13C NMR, IR, EI-MS, and ESI-MS spectroscopy, and in select cases by 31P NMR spectroscopy.

Regioselective Azidation of 2,4-Dichloroquinolines

Reactions of 2,4-dichloroquinolines (2a-f) with sodium azide in DMF lead either regioselectively to 4-azido-2-chloroquinolines (3a-f) or with excess of sodium azide and catalysts to 5-azido-tetrazoloquinolines (4a-f). 2,4-Dichloroquinolines (2g-i) having electron donating substituents in 3-position react with sodium azide in DMF to a mixture of 4-azido-2-chloroquinolines (3g-i) and 5-chlorotetrazoloquinolines (5g-i).When the reaction of the 2,4-dichloroquinolines (2a-i) with sodium azide is carried out in ethanol with addition of methanesulfonic acid, regioselectively 5-chloro-tetrazoloquinolines (5a-i) are obtained.Structural assignments of 3 and 5 have been carried out by 13C-NMR spectra, IR spectra and degradation reactions of the azido- and tetrazolo group to aminoquinolines (7 and 10) via iminophosphoranes (8 and 9).It could be shown that in 2-azido/tetrazolo-quinolines (4 and 5) the tetrazole ring structure is the dominant species.