Pyridine → HCID 117700536, compound

HRID 873525Notes

Reaction equation

HRID 873525 reaction equation
[C:1]1([CH3:11])[CH:6]=CC(S(Cl)(=O)=O)=C[CH:2]=1.[Cl:12][C:13]1[N:18]=[C:17]([C:19]([OH:21])=[O:20])[C:16]([CH3:22])=[CH:15][CH:14]=1.N1C=CC=CC=1.C(=O)([O-])O.[Na+]>C(O)(C)(C)C.O>[Cl:12][C:13]1[N:18]=[C:17]([C:19]([O:21][C:1]([CH3:11])([CH3:6])[CH3:2])=[O:20])[C:16]([CH3:22])=[CH:15][CH:14]=1

Participants

7

Reactant 4

HCID 1049PyridineHCID 73974-Toluenesulfonyl chlorideHCID 516892Sodium BicarbonateHCID 469414706-Chloro-3-methylpyridine-2-carboxylic acid

Product 1

HCID 117700536HCID 117700536, compoundYield 93.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6386tert-ButanolSolvent

Procedure

p-Toluenesulfonyl chloride (10.5 g, 55.1 mmol) was added to a solution of 6-chloro-3-methylpyridine-2-carboxylic acid (4.73 g, 27.6 mmol) as a known compound in tert-butyl alcohol (150 ml) and pyridine (21 ml) at room temperature, and the mixture thus obtained was then stirred at the same temperature as above for 24 hours. Thereafter, a solution of sodium hydrogen carbonate (11.6 g, 138 mmol) in water (300 ml) was added to the resulting solution, and the mixed solution was then stirred. Then, the solvent was distilled away from the reaction solution under reduced pressure. While being washed with water, the solid thus generated was collected by filtration, and was then dried to obtain the title compound (5.85 g, yield: 93%).

Workup

  1. stirringthe mixed solution was then stirred
  2. distillationThen, the solvent was distilled away from the reaction solution under reduced pressure
  3. washWhile being washed with water
  4. filtrationthe solid thus generated was collected by filtration
  5. customwas then dried

Sources & evidence

ORD record
ord-60ce5031baf647128b0b1e1c454c7e81
Source dataset
uspto-grants-2015_03
Patent number
US08975263B2

Reaction notes

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