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Ammonium Chloride → 2-{4-[1-(4-aminophenyl)-3-(trifluoro-methyl)-1H-pyrazol-5-yl]phenyl}ethyl acetate

HRID 351259
Notes
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Reaction equation

HRID 351259 reaction equation
[Cl-].[NH4+].[C:3]([O:6][CH2:7][CH2:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[N:19]([C:20]3[CH:25]=[CH:24][C:23]([N+:26]([O-])=O)=[CH:22][CH:21]=3)[N:18]=[C:17]([C:29]([F:32])([F:31])[F:30])[CH:16]=2)=[CH:11][CH:10]=1)(=[O:5])[CH3:4]>O.CCO.[Fe]>[C:3]([O:6][CH2:7][CH2:8][C:9]1[CH:10]=[CH:11][C:12]([C:15]2[N:19]([C:20]3[CH:25]=[CH:24][C:23]([NH2:26])=[CH:22][CH:21]=3)[N:18]=[C:17]([C:29]([F:31])([F:30])[F:32])[CH:16]=2)=[CH:13][CH:14]=1)(=[O:5])[CH3:4]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 2

HCID 25517Ammonium ChlorideHCID 210907432-{4-[1-(4-nitrophenyl)-3-(trifluoromethyl)-1H-pyrazol-5-yl]phenyl}ethyl acetate

Product 1

HCID 210907062-{4-[1-(4-aminophenyl)-3-(trifluoro-methyl)-1H-pyrazol-5-yl]phenyl}ethyl acetateYield 42.6%

Reagents, catalysts & solvents 3

HCID 23925IronCatalystHCID 702
Ethanol
Solvent
2×
HCID 962WaterSolvent

Procedure

To a solution of ammonium chloride 58.8 mg in H2O 0.5 ml was added iron powder 368 mg and EtOH 2 ml. The reaction mixture was warmed in oil bath, and a solution of 2-{4-[1-(4-nitrophenyl)-3-(trifluoromethyl)-1H-pyrazol-5-yl]phenyl}ethyl acetate 460.7 mg in EtOH 3 ml was added. After being refluxed for 3 hours, the reaction mixture was cooled to ambient temperature and unsoluble matter was removed by filtration. The filtrate was concentrated in vacuo. The residue was dissolved in AcOEt, and washed with saturated aqueous sodium bicarbonate solution and saturated aqueous sodium chloride solution, dried over magnesium sulfate, and concentrated in vacuo. The residue was recrystallized from IPE to give 2-{4-[1-(4-aminophenyl)-3-(trifluoro-methyl)-1H-pyrazol-5-yl]phenyl}ethyl acetate 182.3 mg as a powder.

Workup

  1. temperatureThe reaction mixture was warmed in oil bath
  2. temperatureAfter being refluxed for 3 hours
  3. customunsoluble matter was removed by filtration
  4. concentrationThe filtrate was concentrated in vacuo
  5. dissolutionThe residue was dissolved in AcOEt
  6. washwashed with saturated aqueous sodium bicarbonate solution and saturated aqueous sodium chloride solution
  7. dry with materialdried over magnesium sulfate
  8. concentrationconcentrated in vacuo
  9. customThe residue was recrystallized from IPE

Sources & evidence

ORD record
ord-e96d5054d78e4a79a0c41d1bb87b6d24
Source dataset
uspto-grants-2007_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07183306B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes