Sodium Hydroxide → HCID 22320244, compound

HRID 498058Notes

Reaction equation

HRID 498058 reaction equation
[F:1][C:2]1[C:10]([F:11])=[CH:9][C:5]([C:6](O)=O)=[C:4]([NH:12][C:13]2[N:17]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][N:19]=3)[N:16]=[CH:15][CH:14]=2)[CH:3]=1.P(Cl)(Cl)([Cl:26])=O.[OH-].[Na+]>O>[Cl:26][C:6]1[C:5]2[C:4](=[CH:3][C:2]([F:1])=[C:10]([F:11])[CH:9]=2)[N:12]=[C:13]2[N:17]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][N:19]=3)[N:16]=[CH:15][C:14]=12

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 24813Phosphorus oxychlorideHCID 22320133HCID 22320133, compound

Product 1

HCID 22320244HCID 22320244, compoundYield 57%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of 4,5-difluoro-2-[[1-(2-pyridinyl)-1H-pyrazol-5-yl]amino]benzoic acid (7.00 g, 22.1 mmol) in phosphorous oxychloride (10.3 mL, 111 mmol) was heated under reflux for 1 hour. The solution was allowed to cool to room temperature, and poured into iced water. After neutralization by addition of a sodium hydroxide solution, the organic matter was extracted with chloroform. The extract was washed with saturated brine and water, and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue thus obtained was purified by silica gel column chromatography (chloroform) to give the title compound (3.99 g, 57% yield).

Workup

  1. temperatureunder reflux for 1 hour
  2. extractionthe organic matter was extracted with chloroform
  3. washThe extract was washed with saturated brine and water
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customthe solvent was evaporated under reduced pressure
  6. customThe residue thus obtained
  7. customwas purified by silica gel column chromatography (chloroform)

Sources & evidence

ORD record
ord-1a5c8b76eba04303aad7d51726d38a22
Source dataset
uspto-grants-2005_09
Patent number
US06949648B2

Reaction notes

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