Toluene → HCID 68466152, compound

HRID 1623584Notes

Reaction equation

HRID 1623584 reaction equation
Cl[C:2]1[CH:7]=[CH:6][N+:5]([O-:8])=[C:4]([CH3:9])[C:3]=1[CH3:10].[OH-].[Na+].[CH2:13]([OH:18])[CH2:14][CH2:15][CH2:16][CH3:17].C1(C)C=CC=CC=1>O>[CH2:13]([O:18][C:2]1[CH:7]=[CH:6][N+:5]([O-:8])=[C:4]([CH3:9])[C:3]=1[CH3:10])[CH2:14][CH2:15][CH2:16][CH3:17]

Participants

6

Reactant 4

HCID 1140TolueneHCID 62761-PentanolHCID 14798Sodium HydroxideHCID 98774464-Chloro-2,3-dimethyl-1-oxidopyridin-1-ium

Product 1

HCID 68466152HCID 68466152, compoundYield 125.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

17.0 g (0.11 mol, 1.0 eq.) of 4-chlor-2,3-dimethylpyridine-N-oxide, 8.6 g (0.225 mol, 2.0 eq.) of caustic soda, and 19.0 g (0.22 mol, 2.0 eq.) of 1-pentanol were added to 68 mL of toluene, and the mixture as heated to reflux for 5 hours, and then cooled to room temperature. 15 mL of water was added to the reaction liquid, and the mixture was concentrated, to obtain a residue in the form of a black paste. Subsequently, the residue was dissolved in 500 mL of water, and then the aqueous solution was extracted three times with 670 mL of chloroform. The extract was dried over anhydrous magnesium sulfate, and then concentrated to dryness under reduced pressure, to obtain 28.8 g of 4-pentyloxy-2,3-dimethylpyridine-N-oxide.

Workup

  1. temperaturethe mixture as heated
  2. temperatureto reflux for 5 hours
  3. concentrationthe mixture was concentrated
  4. customto obtain a residue in the form of a black paste
  5. extractionthe aqueous solution was extracted three times with 670 mL of chloroform
  6. dry with materialThe extract was dried over anhydrous magnesium sulfate
  7. concentrationconcentrated to dryness under reduced pressure

Sources & evidence

ORD record
ord-4340fa0c8b6743deb7c185d20f324d8d
Source dataset
uspto-grants-2014_07
Patent number
US08778975B2

Reaction notes

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