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

HRID 1014937Notes

Reaction equation

HRID 1014937 reaction equation
Cl[C:2]1[C:7]([N+:8]([O-])=O)=[CH:6][CH:5]=[CH:4][N:3]=1.Cl.[CH2:12]([O:14][C:15](=[O:18])[CH2:16][NH2:17])[CH3:13].C([O-])([O-])=O.[K+].[K+]>C1(C)C=CC=CC=1>[CH2:12]([O:14][C:15](=[O:18])[CH2:16][NH:17][C:2]1[C:7]([NH2:8])=[CH:6][CH:5]=[CH:4][N:3]=1)[CH3:13]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 796132-Chloro-3-nitropyridineHCID 2723640Glycine ethyl ester, hydrochloride

Product 1

HCID 14390203Ethyl 2-(3-aminopyridin-2-ylamino)acetateYield 71.2%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

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%).

Workup

  1. temperaturewas refluxed overnight
  2. filtrationThe mixture was then filtered
  3. concentrationconcentrated
  4. dissolutionThe resulting yellow solid was dissolved in EtOH (300 mL)
  5. additiontreated with Raney Ni (2 g) and hydrogenated at 40 psi H2 overnight
  6. filtrationThe mixture was filtered
  7. concentrationconcentrated
  8. customchromatographed (2-5% MeOH/CH2Cl2)

Sources & evidence

ORD record
ord-44996e4f5fe84580846f40350f3712d3
Source dataset
uspto-grants-2011_07
Patent number
US07985748B2

Reaction notes

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