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

HRID 82677Notes

Reaction equation

HRID 82677 reaction equation
Cl[C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][CH:5]=[CH:4][N:3]=1.Cl.[NH2:12][CH2:13][C:14]([O:16][CH2:17][CH3:18])=[O:15].C(N(CC)CC)C>CCO>[N+:8]([C:7]1[C:2]([NH:12][CH2:13][C:14]([O:16][CH2:17][CH3:18])=[O:15])=[N:3][CH:4]=[CH:5][CH:6]=1)([O-:10])=[O:9]

Participants

5

Reactant 3

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

Product 1

HCID 14062544Ethyl 2-[(3-nitropyridin-2-YL)amino]acetateYield 74.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 2-chloro-3-nitropyridine (25.3 g) in EtOH (300 mL) were added ethyl 2-aminoacetate hydrochloride (28.7 g) and triethylamine (28.9 mL) at room temperature, and the mixture was refluxed for 1 day. The mixture was concentrated under reduced pressure. The residual crystals were removed by filtration and washed with AcOEt. The filtrate was concentrated under reduced pressure. The residue was purified by column chromatography (silica gel, eluted with 20%-70% AcOEt in hexane). The residual crystals were removed by filtration and washed with IPE. The filtrate was concentrated under reduced pressure to give the title compound (26.9 g).

Workup

  1. temperaturethe mixture was refluxed for 1 day
  2. concentrationThe mixture was concentrated under reduced pressure
  3. customThe residual crystals were removed by filtration
  4. washwashed with AcOEt
  5. concentrationThe filtrate was concentrated under reduced pressure
  6. customThe residue was purified by column chromatography (silica gel, eluted with 20%-70% AcOEt in hexane)
  7. customThe residual crystals were removed by filtration
  8. washwashed with IPE
  9. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-bc836a2193aa495fafcbc1ada322dedc
Source dataset
uspto-grants-2014_09
Patent number
US08846713B2

Reaction notes

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