Water → Methyl 2-chloro-4-(3-Methyl-1H-pyrazol-1-yl)benzoate

HRID 1375382Notes

Reaction equation

HRID 1375382 reaction equation
[Cl:1][C:2]1[CH:11]=[C:10](F)[CH:9]=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5].C(=O)([O-])[O-].[K+].[K+].[CH3:19][C:20]1[CH:24]=[CH:23][NH:22][N:21]=1.O>CN1CCCC1=O>[Cl:1][C:2]1[CH:11]=[C:10]([N:22]2[CH:23]=[CH:24][C:20]([CH3:19])=[N:21]2)[CH:9]=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5]

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 2763551Methyl 2-Chloro-4-fluorobenzoateHCID 178428694HCID 178428694, compound2×

Product 1

HCID 10634466Methyl 2-chloro-4-(3-Methyl-1H-pyrazol-1-yl)benzoate

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
120 °C

Procedure

20.85 g of methyl 2-chloro-4-fluorobenzoate were dissolved in 150 ml of N-methylpyrrolidone, 30.68 g of potassium carbonate and 9.38 ml of 3-methylpyrazole were added thereto, and the mixture was stirred at 120° C. for 3 hours. Additionally, thereto was added 1.79 ml of 3-methylpyrazole, and the mixture was stirred at 120° C. for 3 hours. The reaction solution was cooled, mixed with water, and extracted with EtOAc. The organic layer was washed with water and brine, and then dried over magnesium sulfate. The solvent was evaporated, and then the residue was purified by silica gel column chromatography (hexane-EtOAc (20:1)) to obtain 9.25 g of methyl 2-chloro-4-(3-metyl-1H-pyrazol-1-yl)benzoate.

Workup

  1. stirringthe mixture was stirred at 120° C. for 3 hours
  2. temperatureThe reaction solution was cooled
  3. extractionextracted with EtOAc
  4. washThe organic layer was washed with water and brine
  5. dry with materialdried over magnesium sulfate
  6. customThe solvent was evaporated
  7. customthe residue was purified by silica gel column chromatography (hexane-EtOAc (20:1))

Sources & evidence

ORD record
ord-561ea20210c5454e9773d7050aa0cab2
Source dataset
uspto-grants-2007_01
Patent number
US07169772B2

Reaction notes

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