Hydrochloric Acid → 4-Chloro-2,3-dimethyl-1-oxidopyridin-1-ium

HRID 393361Notes

Reaction equation

HRID 393361 reaction equation
[N+]([C:4]1[CH:9]=[CH:8][N+:7]([O-:10])=[C:6]([CH3:11])[C:5]=1[CH3:12])([O-])=O.[Na+].[Cl-:14].Cl.[OH-].[Na+]>[Cl-].C([N+](CCCC)(CCCC)CCCC)C1C=CC=CC=1.CC#N>[Cl:14][C:4]1[CH:9]=[CH:8][N+:7]([O-:10])=[C:6]([CH3:11])[C:5]=1[CH3:12]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 5234Sodium ChlorideHCID 14798Sodium HydroxideHCID 1482232,3-Dimethyl-4-nitropyridine-N-oxide

Product 1

HCID 98774464-Chloro-2,3-dimethyl-1-oxidopyridin-1-iumYield 99.2%

Reagents, catalysts & solvents 2

HCID 159952Benzyltributylammonium chlorideCatalystHCID 6342AcetonitrileSolvent

Procedure

83.0 g (0.49 mol) of 4-nitro-2,3-dimethylpyridine N-oxide and 90 g (1.54 mol) of NaCl were admixed with 1350 ml of CH3CN, 180 ml of aq. HCl (36%) and 16.6 g of benzyltributylammonium chloride, and the resulting suspension was boiled under reflux with stirring for 12 h. The resulting reaction mixture was adjusted to pH=9 using 350 ml of 20% NaOH, wherefor the existing precipitate largely dissolved. The organic phase was separated off, water was added to the aqueous phase until the precipitate had completely dissolved, and it was subsequently extracted using dichloromethane. The organic phases were combined and the solvent was removed under reduced pressure. 76.6 g (98.5%) of 4-chloro-2,3-dimethylpyridine N-oxide were obtained.

Workup

  1. temperatureunder reflux
  2. customThe resulting reaction mixture
  3. dissolutionwherefor the existing precipitate largely dissolved
  4. customThe organic phase was separated off
  5. additionwater was added to the aqueous phase until the precipitate
  6. dissolutionhad completely dissolved
  7. extractionit was subsequently extracted
  8. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-139fdce91b9641a291345773f725d31a
Source dataset
uspto-grants-2004_10
Patent number
US06806371B2

Reaction notes

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