反应详情

Fuming nitric acid (2.4 ml, 57.9 mmol) was added slowly at 0° C. to a solution of 3-methoxy-4-(3-(pyrrolidin-1-yl)propoxy)benzoic acid hydrochloride (12.15 g, 38.17 mmol) in TFA (40 ml). The cooling bath was removed and the reaction mixture stirred at ambient temperature for 1 hour. The TFA was removed by evaporation and ice/water was added to the residue and the solvent removed by evaporation. The solid residue was dissolved in dilute hydrochloric acid (pH2.2), poured onto a Diaion (trade mark of Mitsubishi) HP20SS resin column and eluted with methanol (gradient 0 to 50%) in water. Concentration of the fractions by evaporation gave a precipitate which was collected by filtration and dried under vacuum over phosphorus pentoxide to give 5-methoxy-2-nitro-4-(3-(pyrrolidin-1-yl)propoxy)benzoic acid hydrochloride (12.1 g, 90%).

1. customThe cooling bath was removed
2. customThe TFA was removed by evaporation and ice/water
3. additionwas added to the residue
4. customthe solvent removed by evaporation
5. dissolutionThe solid residue was dissolved in dilute hydrochloric acid (pH2.2)
6. additionpoured onto a Diaion (trade mark of Mitsubishi) HP20SS resin column
7. washeluted with methanol (gradient 0 to 50%) in water
8. customConcentration of the fractions by evaporation
9. customgave a precipitate which
10. filtrationwas collected by filtration
11. dry with materialdried under vacuum over phosphorus pentoxide