Methyl iodide → HCID 69282792, compound

HRID 915386Notes

Reaction equation

HRID 915386 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[C:10]([CH3:11])=[C:9]([C:12]2[CH:17]=[CH:16][C:15]([Cl:18])=[CH:14][CH:13]=2)[NH:8][N:7]=1)=[O:5])[CH3:2].[OH-].[K+].[CH3:21]I>C(O)C>[CH2:1]([O:3][C:4]([C:6]1[N:7]([CH3:21])[N:8]=[C:9]([C:12]2[CH:13]=[CH:14][C:15]([Cl:18])=[CH:16][CH:17]=2)[C:10]=1[CH3:11])=[O:5])[CH3:2].[CH2:1]([O:3][C:4]([C:6]1[C:10]([CH3:11])=[C:9]([C:12]2[CH:13]=[CH:14][C:15]([Cl:18])=[CH:16][CH:17]=2)[N:8]([CH3:21])[N:7]=1)=[O:5])[CH3:2]

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 14797Potassium HydroxideHCID 178470499HCID 178470499, compound

Product 2

HCID 69282792HCID 69282792, compoundYield 47%HCID 69283012HCID 69283012, compoundYield 36%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

5-(4-Chloro-phenyl)-4-methyl-1H-pyrazole-3-carboxylic acid ethyl ester (58 mg, 0.22 mmol; PCT Int. Appl. (1997), WO 9721682 A1) was added to a solution of KOH (15 mg, 0.27 mmol) in absolute ethanol (1.6 ml). The solution was stirred at ambient temperature for 15 min. Methyl iodide (30 μl, 0.44 mmol) was added and the reaction solution was heated under reflux for 2 h. The solvent was removed under reduced pressure and the residue dissolved in brine/ice water 1/1 and ethyl acetate. The layers were separated and the aqueous layer was extracted two times with ethyl acetate. The combined organic layers were washed with brine and dried over sodium sulfate. The solvent was removed under reduced pressure and the residue purified by column chromatography (silica gel, heptane/AcOEt) to give 29 mg (0.1 mmol, 47%) 5-(4-chloro-phenyl)-2,4-dimethyl-2H-pyrazole-3-carboxylic acid ethyl ester as colorless crystals and 22 mg (0.08 mmol, 36%) 5-(4-chloro-phenyl)-1,4-dimethyl-1H-pyrazole-3-carboxylic acid ethyl ester as colorless crystals.

Workup

  1. temperaturethe reaction solution was heated
  2. temperatureunder reflux for 2 h
  3. customThe solvent was removed under reduced pressure
  4. dissolutionthe residue dissolved in brine/ice water 1/1
  5. customThe layers were separated
  6. extractionthe aqueous layer was extracted two times with ethyl acetate
  7. washThe combined organic layers were washed with brine
  8. dry with materialdried over sodium sulfate
  9. customThe solvent was removed under reduced pressure
  10. customthe residue purified by column chromatography (silica gel, heptane/AcOEt)

Sources & evidence

ORD record
ord-10809cb1c4cf4b11bd7d74c18d8de896
Source dataset
uspto-grants-2007_09
Patent number
US07265149B2

Reaction notes

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