Hydrochloric Acid → HCID 68466331, compound

HRID 1623595Notes

Reaction equation

HRID 1623595 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:22])[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH3:21].Cl>O.C1(C)C=CC=CC=1>[CH2:13]([O:22][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][CH2:20][CH3:21]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 89141-NonanolHCID 14798Sodium HydroxideHCID 98774464-Chloro-2,3-dimethyl-1-oxidopyridin-1-ium

Product 1

HCID 68466331HCID 68466331, compoundYield 159.8%

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 28.9 g (0.2 mol, 2.0 eq.) of 1-nonanol were added to 64 mL of toluene, and the mixture was heated to reflux for 4 hours, and then cooled to room temperature. 160 mL of water was added to the reaction liquid, and then the mixture was neutralized with concentrated hydrochloric acid (8.5 g). Subsequently, the resultant was extracted with 160 mL of ethyl acetate. The extract was dried over anhydrous magnesium sulfate, and then concentrated under reduced pressure, to obtain 42.4 g of 4-nonyloxy-2,3-dimethylpyridine-N-oxide as a black brown oily matter.

Workup

  1. temperaturethe mixture was heated
  2. temperatureto reflux for 4 hours
  3. extractionSubsequently, the resultant was extracted with 160 mL of ethyl acetate
  4. dry with materialThe extract was dried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-de61b30b842b40c89e09baf7af589d54
Source dataset
uspto-grants-2014_07
Patent number
US08778975B2

Reaction notes

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