Sodium Hydroxide → HCID 22036982, compound

Participants

Reaction Steps

Phosphorus tribromide (0.0105 mol) was added dropwise at 0° C./5° C. under N2 flow to a mixture of (±)-5,6,7,8-tetrahydro-2-methyl-8-quinolinol (intermediate 17) (0.03 mol) in toluene (20 ml). The mixture was brought to room temperature and stirred at room temperature overnight. Ice water was added. The mixture was basified with a concentrated NaOH solution and extracted with CH2Cl2. The organic layer was separated, dried (MgSO4), filtered and the solvent was evaporated. The residue (6 g) was purified by column chromatography over silica gel (eluent: CH2Cl2/CH3OH 99/1; 20–45 μm). The pure fractions were collected and the solvent was evaporated, yielding 2 g (29%) of (±)-8-bromo-5,6,7,8-tetrahydro-2-methylquinoline (interm. 18).

Provenance & Evidence