Water → HCID 178437185, compound

Participants

Reaction Steps

1-Quinolin-8-yl-1-(1-trityl-1H-imidazol-4-yl)-ethanol (Intermediate C1) and p-toluenesulfonic acid catalyst in toluene was heated to reflux in a Dean-Stark apparatus for 18 h. The mixture was cooled to rt and freed of solvent. The residue was dissolved in 70% acetic acid:water and heated to 100° C. for 1 h. The reaction mixture was cooled to rt and basified with 2 M NaOH and extracted with chloroform:isopropyl alcohol (3:1). The organic layers were pooled, dried over MgSO4, filtered and concentrated onto silica gel. The product was eluted from a column of silica gel with 4% NH3-MeOH:CH2Cl2 to give 8-[1-(1H-imidazol-4-yl)-vinyl]-quinoline.

Provenance & Evidence