反応 #2446074

反応方程式

2-Chloromethylpyridine hydrochloride

glycin

NaOH

→

(Bis(2-pyridylmethyl)amino)acetic Acid

溶媒

water

反応条件

後処理

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

実験手順

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).

出典