Hydrochloric Acid → HCID 68466746, compound

HRID 1623592Notes

Reaction equation

HRID 1623592 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:21])[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH3:20].Cl>O.C1(C)C=CC=CC=1>[CH2:13]([O:21][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][CH2:17][CH2:18][CH2:19][CH3:20]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 9571-OctanolHCID 14798Sodium HydroxideHCID 98774464-Chloro-2,3-dimethyl-1-oxidopyridin-1-ium

Product 1

HCID 68466746HCID 68466746, compoundYield 155.9%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

15.8 g (0.1 mol, 1.0 eq.) of 4-chlor-2,3-dimethylpyridine-N-oxide, 8.0 g (0.2 mol, 2.0 eq.) of caustic soda, and 26.0 g (0.2 mol, 2.0 eq.) of 1-octanol were added to 64 mL of toluene, and the mixture was heated to reflux for 3 hours, and then cooled to room temperature. 15 mL of water was added to the reaction liquid, and then the mixture was neutralized with concentrated hydrochloric acid (8 mL). Subsequently, the resultant 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 39.2 g of 4-octyloxy-2,3-dimethylpyridine-N-oxide as a black brown oily matter.

Workup

  1. temperaturethe mixture was heated
  2. temperatureto reflux for 3 hours
  3. extractionSubsequently, the resultant was extracted three times with 670 mL of chloroform
  4. dry with materialThe extract was dried over anhydrous magnesium sulfate
  5. concentrationconcentrated to dryness under reduced pressure

Sources & evidence

ORD record
ord-91076926465543c4a66203bd0a7fde16
Source dataset
uspto-grants-2014_07
Patent number
US08778975B2

Reaction notes

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