Triethylamine → Ethyl 2-[(3-nitropyridin-2-YL)amino]acetate

HRID 2351587Notes

Reaction equation

HRID 2351587 reaction equation
Cl[C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[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(N(CC)CC)C>C(O)C>[CH2:12]([O:14][C:15](=[O:18])[CH2:16][NH:17][C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][CH:5]=[CH:4][N:3]=1)[CH3:13]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 796132-Chloro-3-nitropyridineHCID 2723640Glycine ethyl ester, hydrochloride

Product 1

HCID 14062544Ethyl 2-[(3-nitropyridin-2-YL)amino]acetate

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 2-chloro-3-nitropyridine (50 g, 0.315 mole), glycine ethyl ester hydrochloride (220 g, 1.58 mole), and triethylamine, (155 g, 1.53 mole) in 1 liter of absolute ethanol was stirred and heated to reflux overnight. The reaction mixture was evaporated to a solid mass, which was partitioned between water and ethyl acetate. The aqueous layer was separated and extracted with ethyl acetate (3×). The combined ethyl acetate layer was evaporated to an oil, which was dried by azeotropic distillation with benzene. The residue was purified by silica gel chromatography (8 cm×27 cm column) by elution with 5% methanol/95% benzene. The appropriate fractions totaled 59.2 g of the title product, m.p. 38°-9° C.

Workup

  1. temperatureheated
  2. temperatureto reflux overnight
  3. customThe reaction mixture was evaporated to a solid mass, which
  4. customwas partitioned between water and ethyl acetate
  5. customThe aqueous layer was separated
  6. extractionextracted with ethyl acetate (3×)
  7. customThe combined ethyl acetate layer was evaporated to an oil, which
  8. dry with materialwas dried by azeotropic distillation with benzene
  9. customThe residue was purified by silica gel chromatography (8 cm×27 cm column) by elution with 5% methanol/95% benzene

Sources & evidence

ORD record
ord-20872efc877b4f8b85a8dd20e75376b3
Source dataset
uspto-grants-1989_10
Patent number
US04873251

Reaction notes

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