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o-Chlorophenylacetic acid → HCID 69007338, compound

HRID 1635921
Notes
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Reaction equation

HRID 1635921 reaction equation
[NH2:1][C:2]1[C:6]([C:7]2[CH:12]=[CH:11][N:10]=[CH:9][CH:8]=2)=[C:5]([C:13]2[CH:18]=[CH:17][C:16]([F:19])=[CH:15][CH:14]=2)[NH:4][N:3]=1.P(Cl)(Cl)[Cl:21].Cl[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=1[CH2:31][C:32]([OH:34])=O>N1C=CC=CC=1>[Cl:21][CH:31]([C:26]1[CH:27]=[CH:28][CH:29]=[CH:30][CH:25]=1)[C:32]([NH:1][C:2]1[C:6]([C:7]2[CH:12]=[CH:11][N:10]=[CH:9][CH:8]=2)=[C:5]([C:13]2[CH:18]=[CH:17][C:16]([F:19])=[CH:15][CH:14]=2)[NH:4][N:3]=1)=[O:34]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 17124o-Chlorophenylacetic acidHCID 24387Phosphorus trichlorideHCID 155131013-Amino-5-(4-fluorophenyl)-4-(4-pyridyl)pyrazole

Product 1

HCID 69007338HCID 69007338, compoundYield 42.1%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

150 mg of 3-amino-5-(4-fluorophenyl)-4-(4-pyridyl)pyrazole was dispersed in 6 ml of pyridine. While this dispersion was being cooled on a salt-ice bath, 122 mg of phosphorus trichloride was added thereto with stirring. After the resulting mixture was stirred at the same temperature for 25 minutes, 335 mg of 2-chlorophenylacetic acid was added thereto, followed by stirring at room temperature for 20 hours. After the pyridine was distilled off under reduced pressure, the residue was extracted with methanol and chloroform. After the organic layer was washed with water and dried over anhydrous magnesium sulfate, the solvent was distilled off under reduced pressure. The resulting residue was purified by column chromatography using 80 g of silica gel [with an elution solvent comprising chloroform-methanol (30:1)]. Thus, 101 mg (42% yield) of the title compound was obtained.

Workup

  1. temperatureWhile this dispersion was being cooled on a salt-ice bath
  2. stirringAfter the resulting mixture was stirred at the same temperature for 25 minutes
  3. stirringby stirring at room temperature for 20 hours
  4. distillationAfter the pyridine was distilled off under reduced pressure
  5. extractionthe residue was extracted with methanol and chloroform
  6. washAfter the organic layer was washed with water
  7. dry with materialdried over anhydrous magnesium sulfate
  8. distillationthe solvent was distilled off under reduced pressure
  9. customThe resulting residue was purified by column chromatography

Sources & evidence

ORD record
ord-2b6dfc5122e34dafbe5bed1c41864d25
Source dataset
uspto-grants-2003_01
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06511997B1

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes