Hydrochloric Acid → 1,2,3,4-Tetrahydro-7-nitroisoquinoline

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Reaction Steps

Sulfuric acid (9.90 mL, 0.186 mol) was cooled to 0° C. To the cooled solution was added 1,2,3,4-Tetrahydroisoquinoline (2.5 mL, 020.0 mmol) dropwise via syringe. Potassium nitrate (2.16 g, 0.0214 mol) was then added in small portions over 4 min. The cooling bath was removed and the mixture was allowed to stir at rt for 12 h. Ice was added to the slurry and the mixture basified with NH4OH (precipitate formed). The solution was extracted with chloroform, dried over Na2SO4, filtered, and concentrated to give a brown oil. The oil was dissolved in ethanol (14.8 mL, 0.254 mol) and to this solution was added HCl (2.47 mL, 0.0808 mol). Additional EtOH was added to transfer the precipitated solid for filtration. The white solid was dried under vacuum to yield the desired product without further purification (2.19 g, 51%)

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