Tert-Butylamine → Methyl 1-(t-butylamino)isoquinoline-5-carboxylate

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Reaction Steps

5-(Methoxycarbonyl)isoquinoline 2-oxide (2.0 g, 9.84 mmol) obtained in Step (4) above and trifluorotoluene (20 mL) were mixed and stirred. The reaction solution was slowly added with t-butylamine (3.6 g, 49.25 mmol) and p-toluenesulfonic acid anhydride (6.42 g, 19.68 mmol) at about 5° C., and stirred for about 2 hours at the same temperature (˜5° C.). The reaction mixture was diluted with ethyl acetate, and washed with a saturated aqueous sodium bicarbonate solution and saline. The organic layer thus obtained was dried over anhydrous sodium sulfate, filtered, and concentrated under reduced pressure to obtain the title compound (1.6 g, 64%).

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