反应 #1256721

反应方程式

2-Chloromethylpyridine hydrochloride

glycin

NaOH

→

(Bis(2-pyridylmethyl)amino)acetic Acid

溶剂

water

反应条件

后处理

1. 1
   温度to maintain the pH at 8-10
2. 2
   萃取The resulting dark red solution was extracted with ethyl acetate
3. 3
   浓缩concentrated
4. 4
   workup.DISSOLUTIONThe residue was dissolved in dichloromethane
5. 5
   过滤the insoluble sodium chloride was filtered
6. 6
   其他Pale yellow crystals formed from the filtrate, which
7. 7
   其他were collected
8. 8
   其他dried under vacuum
9. 9
   其他Yield (2.87 g) (11.2 mmol, 42%)

实验过程

2-Chloromethylpyridine hydrochloride (9.2 g, 8.53 mmol) and glycin (2 g, 26.6 mmol) were dissolved in water (30 mL) and stirred at room temperature for five days, with addition of 5 mol aqueous NaOH solution at intervals to maintain the pH at 8-10. The resulting dark red solution was extracted with ethyl acetate, neutralized with HCl and concentrated. The residue was dissolved in dichloromethane, and the insoluble sodium chloride was filtered. Pale yellow crystals formed from the filtrate, which were collected and dried under vacuum. Yield (2.87 g) (11.2 mmol, 42%). 1H NMR (CDCl3), 300 MHz): 3.39 (s, 2H), 3.98 (s, 4H), 7.06 (t, 2H), 7.30 (d, 2H), 7.56 (t, 2H), 8.36 (d, 2H). 13C NMR (CD3OD, 300 MHz): 57.36 (C, CH2), 59.77 (2C, PyCH2), 124.77 (2CH, Py), 125.15 (2CH, Py), 139.00 (C, CH2), 149.76 (2CH, Py), 156.10 (2C, Py), 173.05 (C, CO2H).

来源