Water → 4-Methyl-5-nitro-2-phenoxy-pyridine

HRID 491863Notes

Reaction equation

HRID 491863 reaction equation
Cl[C:2]1[CH:7]=[C:6]([CH3:8])[C:5]([N+:9]([O-:11])=[O:10])=[CH:4][N:3]=1.[C:12]1([OH:18])[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.C(=O)([O-])[O-].[K+].[K+].O>CN(C=O)C>[CH3:8][C:6]1[C:5]([N+:9]([O-:11])=[O:10])=[CH:4][N:3]=[C:2]([O:18][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH:7]=1

Participants

6

Reactant 4

HCID 962WaterHCID 996PhenolHCID 11430Potassium CarbonateHCID 3453642-Chloro-4-methyl-5-nitropyridine

Product 1

HCID 576783574-Methyl-5-nitro-2-phenoxy-pyridine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
110 °C

Procedure

A solution of 2-chloro-4-methyl-5-nitropyridine (10 g, 0.058 mol), in DMF (100 mL) was treated with phenol (6.6 g, 0.07 mol) and potassium carbonate (9.6 g, 0.07 mol) and the reaction mixture was stirred at 110° C. for 4 hr and then cooled. To the reaction mixture was then added water. The reaction mixture was extracted into EtOAc, dried and concentrated to a syrup, which was purified via column chromatography (4:2:0.5; CHCl3:hexanes:EtOAc, v/v) to yield 4-methyl-5-nitro-2-phenoxy-pyridine as a light yellow solid.

Workup

  1. temperaturecooled
  2. extractionThe reaction mixture was extracted into EtOAc
  3. customdried
  4. concentrationconcentrated to a syrup, which
  5. customwas purified via column chromatography (4:2:0.5; CHCl3:hexanes:EtOAc, v/v)

Sources & evidence

ORD record
ord-5d225417468b4b9e84291623bb4f895c
Source dataset
uspto-grants-2009_05
Patent number
US07531545B2

Reaction notes

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