Reaction #1256721

Reaction equation

2-Chloromethylpyridine hydrochloride

glycin

NaOH

→

(Bis(2-pyridylmethyl)amino)acetic Acid

Solvents

water

Conditions

Workup

1. 1
   Temperatureto maintain the pH at 8-10
2. 2
   ExtractionThe resulting dark red solution was extracted with ethyl acetate
3. 3
   Concentrationconcentrated
4. 4
   workup.DISSOLUTIONThe residue was dissolved in dichloromethane
5. 5
   Filtrationthe insoluble sodium chloride was filtered
6. 6
   OtherPale yellow crystals formed from the filtrate, which
7. 7
   Otherwere collected
8. 8
   Otherdried under vacuum
9. 9
   OtherYield (2.87 g) (11.2 mmol, 42%)

Procedure

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).

Source