Sodium Chloride → Pyridine, 2,3-dimethyl-, 1-oxide

HRID 1444736Notes

Reaction equation

HRID 1444736 reaction equation
O.O.O.O.O.O.C(O[O-])(=O)C1C(=CC=CC=1)C([O-])=[O:11].[Mg+2].[CH3:21][C:22]1[C:27]([CH3:28])=[CH:26][CH:25]=[CH:24][N:23]=1.C(=O)([O-])[O-].[K+].[K+].[Cl-].[Na+]>O>[CH3:21][C:22]1[C:27]([CH3:28])=[CH:26][CH:25]=[CH:24][N+:23]=1[O-:11]

Participants

6

Reactant 4

HCID 5234Sodium ChlorideHCID 114202,3-LutidineHCID 11430Potassium Carbonate2×HCID 21894687Magnesium 2-(dioxidan-2-ide-1-carbonyl)benzoate--water (1/1/6)

Product 1

HCID 3840573Pyridine, 2,3-dimethyl-, 1-oxideYield 97%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Conditions

Temperature
27.5 °C

Procedure

46.2 g of magnesium monoperoxyphthalate hexahydrate in 150 ml of water were slowly added at room temperature to a solution of 11.32 ml (0.100 mole) of 2,3-dimethylpyridine and 11.2 g of potassium carbonate in 50 ml of water. The reaction was carried out at a pH of 6.5-7.0, adjusted by a solution of potassium carbonate, and the reaction mixture was stirred for three hours at a temperature of from 25 to 30° C. At the end of the reaction, the pH was adjusted to 7.5-8.0, 40 g of sodium chloride were added and the 2,3-dimethylpyridine N-oxide was extracted with methylene chloride. The extraction was repeated from saturated reaction solution. The combined organic phases were dried with sodium sulphate and concentrated to a volume of 60 ml. The yield was 97-98%, determined by HPLC.

Workup

  1. customAt the end of the reaction
  2. additionwere added
  3. extractionthe 2,3-dimethylpyridine N-oxide was extracted with methylene chloride
  4. extractionThe extraction
  5. dry with materialThe combined organic phases were dried with sodium sulphate
  6. concentrationconcentrated to a volume of 60 ml

Sources & evidence

ORD record
ord-3737a50aecda4f91b207bd3b462e1369
Source dataset
uspto-grants-2010_02
Patent number
US07662968B2

Reaction notes

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