反应详情

4-Bromomethyl-3-nitrobenzoic acid (10 g) is dissolved in dichloromethane (100 ml) and thereto is added dropwise pyrrolidine (8 g) with stirring under ice cooling, and the mixture is stirred at room temperature for 30 minutes. Dichloromethane is distilled off under reduced pressure, and the residue is dissolved in conc. hydrochloric acid (40 ml) and thereto is added water (10 ml) with stirring under ice cooling and further is added tin (5.4 g), and the mixture is stirred under ice cooling for 1.5 hour. The reaction mixture is neutralized with 10N aqueous sodium hydroxide solution, and the catalyst is filtered off and the filtrate is concentrated. The residue is dissolved in water and purified by a medium pressure column chromatography with CHP-20P (eluant, water-acetonitrile). The fractions containing the desired compound are collected, and concentrated into dryness under reduced pressure to give 3-amino-4-(1-pyrrolidinylmethyl)benzoic acid (7.2 g).

1. stirringthe mixture is stirred at room temperature for 30 minutes
2. distillationDichloromethane is distilled off under reduced pressure
3. dissolutionthe residue is dissolved in conc. hydrochloric acid (40 ml)
4. additionis added water (10 ml)
5. stirringwith stirring under ice cooling
6. additionfurther is added tin (5.4 g)
7. stirringthe mixture is stirred under ice cooling for 1.5 hour
8. filtrationthe catalyst is filtered off
9. concentrationthe filtrate is concentrated
10. dissolutionThe residue is dissolved in water
11. custompurified by a medium pressure column chromatography with CHP-20P (eluant, water-acetonitrile)
12. additionThe fractions containing the desired compound
13. customare collected
14. concentrationconcentrated into dryness under reduced pressure