Potassium Carbonate → Ethyl 2-(3-aminopyridin-2-ylamino)acetate

Participants

Reaction Steps

A mixture of 2-chloro-3-nitropyridine (9.4 g, 59 mmol), glycine ethyl ester hydrochloride (10.8 g, 77 mmol), and K2CO3 (21.3 g, 154 mmol) in toluene (100 mL) was refluxed overnight. The mixture was then filtered, concentrated, and subjected to chromatography (20% EtOAc/hexanes). The resulting yellow solid was dissolved in EtOH (300 mL), treated with Raney Ni (2 g) and hydrogenated at 40 psi H2 overnight. The mixture was filtered, concentrated and chromatographed (2-5% MeOH/CH2Cl2) to provide 34A (1.25 g, 14%) and N-(3-amino-2-pyridinyl)glycine ethyl ester (8.2 g, 71%).

Provenance & Evidence