Hydrochloric Acid → HCID 68468429, compound

HRID 1623590Notes

Reaction equation

HRID 1623590 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:20])[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH3:19].Cl>O.C1(C)C=CC=CC=1>[CH2:13]([O:20][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][CH3:19]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 8129HeptanolHCID 14798Sodium HydroxideHCID 98774464-Chloro-2,3-dimethyl-1-oxidopyridin-1-ium

Product 1

HCID 68468429HCID 68468429, compoundYield 157.2%

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 23.2 g (0.2 mol, 2.0 eq.) of 1-heptanol 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 under reduced pressure, to obtain 37.3 g of 4-heptyloxy-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 under reduced pressure

Sources & evidence

ORD record
ord-f4d897a26fb14dd6bb895146232c4605
Source dataset
uspto-grants-2014_07
Patent number
US08778975B2

Reaction notes

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