Methanol → N-{2-[(5-nitro-2-pyridinyl)amino]ethyl}acetamide

HRID 1359019Notes

Reaction equation

HRID 1359019 reaction equation
[NH2:1][CH2:2][CH2:3][NH:4][C:5]1[CH:10]=[CH:9][C:8]([N+:11]([O-:13])=[O:12])=[CH:7][N:6]=1.[C:14](OC(=O)C)(=[O:16])[CH3:15].CO>C(Cl)(Cl)(Cl)Cl>[C:14]([NH:1][CH2:2][CH2:3][NH:4][C:5]1[CH:10]=[CH:9][C:8]([N+:11]([O-:13])=[O:12])=[CH:7][N:6]=1)(=[O:16])[CH3:15]

Participants

5

Reactant 3

HCID 887MethanolHCID 7918Acetic AnhydrideHCID 1224252-(2-Aminoethylamino)-5-nitropyridine

Product 1

HCID 2901081N-{2-[(5-nitro-2-pyridinyl)amino]ethyl}acetamideYield 81.7%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

A suspension of 2-(2-aminoethylamino)-5-nitropyridine (5.0 g, 27.47 mmol) in carbon tetrachloride (60 ml) was treated with acetic anhydride (5.6 g, 54.9 mmol) and methanol (0.5 ml) and the resulting mixture was refluxed for 2 h then allowed to cool to room temperature. The mixture was filtered and the residue partitioned between 1M sodium hydroxide and CH2Cl2. The organic phase was dried (MgSO4) and concentrated to afford the title compound (5.03 g) as a buff solid m.p. 177-180°. MS(ES+) 225 (MH+).

Workup

  1. temperaturethe resulting mixture was refluxed for 2 h
  2. filtrationThe mixture was filtered
  3. customthe residue partitioned between 1M sodium hydroxide and CH2Cl2
  4. dry with materialThe organic phase was dried (MgSO4)
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-e67adcb773f04caa97417e08fa1f77fc
Source dataset
uspto-grants-2003_07
Patent number
US06599908B1

Reaction notes

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