Sodium Hydroxide → 3-[(4-Fluorophenyl)methoxy]-4-nitropyridine

HRID 1982893Notes

Reaction equation

HRID 1982893 reaction equation
P(Cl)(Cl)Cl.[F:5][C:6]1[CH:23]=[CH:22][C:9]([CH2:10][O:11][C:12]2[CH:13]=[N+:14]([O-])[CH:15]=[CH:16][C:17]=2[N+:18]([O-:20])=[O:19])=[CH:8][CH:7]=1.[OH-].[Na+]>C(OCC)(=O)C>[F:5][C:6]1[CH:23]=[CH:22][C:9]([CH2:10][O:11][C:12]2[CH:13]=[N:14][CH:15]=[CH:16][C:17]=2[N+:18]([O-:20])=[O:19])=[CH:8][CH:7]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 24387Phosphorus trichlorideHCID 675273003-[(4-Fluorophenyl)methoxy]-4-nitro-1-oxo-1lambda~5~-pyridine

Product 1

HCID 675283513-[(4-Fluorophenyl)methoxy]-4-nitropyridine

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Phosphorus trichloride (3.65 ml, 41.80 mmol) was slowly added at 0° C. to a solution of 3-(4-fluorobenzyloxy)-4-nitropyridin-N-oxide (7.72 g, 27.87 mmol) prepared in Step 3 in 500 ml of ethyl acetate. The reaction mixture was stirred for 1 hour at room temperature and then alkalized with 2N sodium hydroxide solution. The separated organic layer was dried on anhydrous magnesium sulfate and then concentrated under reduced pressure. The resulting residue was used in the subsequent step without further purification.

Workup

  1. dry with materialThe separated organic layer was dried on anhydrous magnesium sulfate
  2. concentrationconcentrated under reduced pressure
  3. customThe resulting residue was used in the subsequent step without further purification

Sources & evidence

ORD record
ord-2138dd5caf904ac38b4806ef86ecbce3
Source dataset
uspto-grants-2009_06
Patent number
US07541366B2

Reaction notes

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