Dimethylformamide → HCID 22380321, compound

HRID 895534Notes

Reaction equation

HRID 895534 reaction equation
F[C:2]1[C:3]([N+:8]([O-:10])=[O:9])=[N:4][CH:5]=[CH:6][CH:7]=1.C[N:12]([CH:14]=O)C.[CH2:16]1COCC1>O>[CH2:14]([NH:12][C:2]1[C:3]([N+:8]([O-:10])=[O:9])=[N:4][CH:5]=[CH:6][CH:7]=1)[CH3:16]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 8028TetrahydrofuranHCID 27628023-Fluoro-2-nitropyridine

Product 1

HCID 22380321HCID 22380321, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Ice cold ethylamine (0.55 mL) was added to a solution of 3-fluoro-2-nitropyridine (400 mg, 2.8 mmol; prepared according to N. Plé and G. Quéguiner, J. Heterocyclic Chem, 1989, 26, 475-476) in 2:1 DMF:THF (6 mL) at ambient temperature, and the mixture stirred for 0.75 h. Water was added, then extracted 2× with ethyl acetate. The combined organic layers were washed with water then with saturated aqueous sodium chloride, dried (MgSO4), and concentrated to give 3-ethylamino-2-nitro-pyridine as a gold solid. 1H NMR (CDCl3): δ 7.87 (d, 1h0, 7.43 (dd, 1H), 7.35 (d, 1H), 3.38 (pentet, 2H), 1.4 (t, 3H). LCMS: 121.1(MH+-NO2).

Workup

  1. extractionextracted 2× with ethyl acetate
  2. washThe combined organic layers were washed with water
  3. dry with materialwith saturated aqueous sodium chloride, dried (MgSO4)
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-7eeaa8eeb56d4c3b943f70e07ff87432
Source dataset
uspto-grants-2005_07
Patent number
US06916819B2

Reaction notes

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