Nitrogen → Bis(1-isoquinolyl)amine

참여 물질

반응 단계

To a 100-mL round-bottom flask were added 1-chloroisoquinoline (2.84 g, 17.3 mmol), 1-aminoisoquinoline (2.5 g, 17.3 mmol), sodium tert-butoxide (2.33 g, 24.3 mmol), palladium (II) acetate (0.16 g, 0.69 mmol), bis(2-diphenylphosphinophenyl)ether(0.35 g, 0.65 mmol), and toluene (40 mL sparged with N2). The reaction mixture was heated at 105° C. for 18 h under an atm of N2. The reaction mixture was diluted with ether and THF, and washed with water. This solution was passed through a pad of celite to remove insoluble particles. The organic layer was dried over MgSO4 and then passed through a plug of SiO2 gel eluting with CH2Cl2:CH3CN 90:10. The volatile components were removed with a rotary evaporator to afford 4.46 g (94.9%) of bis(1-isoquinolyl)amine as an olive powder. Results of 1H NMR spectroscopy and electrospray mass spectroscopy are consistent with the product. 1H NMR (300 MHz, CDCl3): δ 6.93 (d, J=6.4 Hz, 2H), 7.63 (m, 7H), 7.71 (d, J=6.4 Hz, 2H), 9.11 (d, J=7.9 Hz, 2H).

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