Water → HCID 22036991, compound

Participants

Reaction Steps

A dispersion of sodium hydride in mineral oil (0.261 mol) was added portionwise at room temperature under N2 flow to a mixture of N-8-quinolinylformamide (0.174 mol) in DMF (500 ml). The mixture was stirred at room temperature for 1 hour. A solution of 1-chloro-2-nitrobenzene (0.53 mol) in DMF (200 ml) was added dropwise. The mixture was stirred at 140° C. for 12 hours and then brought to room temperature. H2O was added and the mixture was extracted with CH2Cl2. The organic layer was separated, dried (MgSO4), filtered and the solvent was evaporated. The residue (110 g) was purified by column chromatography over silica gel (eluent: CH2Cl2/cyclohexane 80/20; 20-45 μm). The pure fractions were collected and the solvent was evaporated, yielding 9.8 g (21%) of N-(2-nitrophenyl)-8-quinolinamine (interm. 23).

Provenance & Evidence