반응 #2446074

반응 방정식

2-Chloromethylpyridine hydrochloride

glycin

NaOH

→

(Bis(2-pyridylmethyl)amino)acetic Acid

용매

water

반응 조건

후처리

1. 1
   온도to maintain the pH at 8-10
2. 2
   추출The resulting dark red solution was extracted with ethyl acetate
3. 3
   농축concentrated
4. 4
   workup.DISSOLUTIONThe residue was dissolved in dichloromethane
5. 5
   여과the insoluble sodium chloride was filtered
6. 6
   기타Pale yellow crystals formed from the filtrate, which
7. 7
   기타were collected
8. 8
   기타dried under vacuum
9. 9
   기타Yield (2.87 g) (11.2 mmol, 42%)

실험 절차

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).

출처