Potassium Iodide → HCID 86692553, compound

HRID 1748600Notes

Reaction equation

HRID 1748600 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[CH:7]=[N:8][N:9]([C:12]2[CH:17]=[C:16]([CH3:18])[C:15](N)=[CH:14][N:13]=2)[C:10]=1[CH3:11])=[O:5])[CH3:2].N([O-])=O.[Na+].[I-:24].[K+].C(=O)([O-])[O-].[Na+].[Na+]>S(=O)(=O)(O)O.O>[CH2:1]([O:3][C:4]([C:6]1[CH:7]=[N:8][N:9]([C:12]2[CH:17]=[C:16]([CH3:18])[C:15]([I:24])=[CH:14][N:13]=2)[C:10]=1[CH3:11])=[O:5])[CH3:2]

Participants

7

Reactant 4

HCID 4875Potassium IodideHCID 10340Sodium CarbonateHCID 23668193Sodium NitriteHCID 86692551HCID 86692551, compound

Product 1

HCID 86692553HCID 86692553, compoundYield 81.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1118Sulfuric AcidSolvent

Procedure

1-(5-Amino-4-methylpyridin-2-yl)-5-methyl-1H-pyrazole-4-carboxylic acid ethyl ester (1.0 g) was suspended in 20% (v/v) sulfuric acid aqueous solution (75 ml), sodium nitrite (318 mg) was added thereto little by little under ice-cooling with stirring, and then stirred for 40 minutes under ice-cooling. Then, potassium iodide (1.27 g) was dissolved in water (12 ml), and the obtained aqueous solution was slowly added dropwise to the reaction solution under ice-cooling with stirring. After the completion of adding dropwise, the solution was stirred for 3 hours under ice-cooling, and then gradually warmed to room temperature. The reaction solution was poured into 10% sodium carbonate aqueous solution, the precipitated solid was collected by filtration, and dissolved in ethyl acetate. The organic layer was sequentially washed with sodium thiosulfate aqueous solution, water, and saturated brine, dried over anhydrous sodium sulfate, and then the solvent was evaporated to give 1-(5-iodo-4-methylpyridin-2-yl)-5-methyl-1H-pyrazole-4-carboxylic acid ethyl ester (1.16 g) as a brown solid.

Workup

  1. temperaturelittle by little under ice-cooling
  2. stirringstirred for 40 minutes under ice-
  3. temperaturecooling
  4. additionthe obtained aqueous solution was slowly added dropwise to the reaction solution under ice-
  5. temperaturecooling
  6. stirringwith stirring
  7. additionAfter the completion of adding dropwise
  8. stirringthe solution was stirred for 3 hours under ice-
  9. temperaturecooling
  10. filtrationthe precipitated solid was collected by filtration
  11. dissolutiondissolved in ethyl acetate
  12. washThe organic layer was sequentially washed with sodium thiosulfate aqueous solution, water, and saturated brine
  13. dry with materialdried over anhydrous sodium sulfate
  14. customthe solvent was evaporated

Sources & evidence

ORD record
ord-23b31b0337c64372b78852a5f264b843
Source dataset
uspto-grants-2015_10
Patent number
US09150555B2

Reaction notes

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