Dimethylacetamide → HCID 68993145, compound

Participants

Reaction Conditions

Reaction Steps

4-Chloro-6,7-dimethoxyquinoline (2.0 g, 9.0 mmol) was dissolved in N,N-dimethylacetamide (12 ml). The mixture was degassed under nitrogen. Zinc(II) cyanide (0.66 g, 5.8 mml), zinc (0.084 g, 1.3 mmol), tris(dibenzylidene-acetone)dipalladium(0) (0.17 g, 0.19 mmol) and 1,1′-bis(diphenylphosphino)ferrocene (0.23 g, 0.41 mmol) were then added. The reaction mixture was heated in a microwave at 150° C. for 10 minutes. The solvent was removed and the residue was purified by silica gel chromatography (hexane to ethyl acetate) to give 6,7-dimethoxyquinoline-4-carbonitrile that was dissolved in 5% hydrochloric acid (conc) in ethanol and stirred under a hydrogen balloon with Pd/C (cat.). After filtration through celite, the filtrate was collected and concentrated to give (6,7-dimethoxyquinolin-4-yl)methanaminium chloride. MS (ESI, pos. ion) m/z: 219 (M+1).

Provenance & Evidence