Sodium Hydroxide → HCID 22320298, compound

HRID 498046Notes

Reaction equation

HRID 498046 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[N:7]1[C:11]([NH:12][C:13]2[CH:21]=[CH:20][CH:19]=[CH:18][C:14]=2[C:15](O)=O)=[CH:10][CH:9]=[N:8]1.P(Cl)(Cl)([Cl:24])=O.[OH-].[Na+]>O>[Cl:24][C:15]1[C:14]2[C:13](=[CH:21][CH:20]=[CH:19][CH:18]=2)[N:12]=[C:11]2[N:7]([C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][N:1]=3)[N:8]=[CH:9][C:10]=12

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 24813Phosphorus oxychlorideHCID 22320218HCID 22320218, compound

Product 1

HCID 22320298HCID 22320298, compoundYield 76.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of 2-[[1-(2-pyridinyl)-1H-pyrazol-5-yl]amino]benzoic acid (62.0 g, 0.221 mol) in phosphorous oxychloride (166 g, 1.08 mol) was heated under reflux for 1 hour. The solution was allowed to cool to room temperature and poured into water. The solution was neutralized by addition of a sodium hydroxide solution, and 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 (47.4 g, 76% 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-c3f8534e1ab44a9e96416a286bdf2909
Source dataset
uspto-grants-2005_09
Patent number
US06949648B2

Reaction notes

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