Acetic Acid → 2-{4-[1-(4-nitrophenyl)-3-(trifluoromethyl)-1H-pyrazol-5-yl]phenyl}ethyl acetate

HRID 351258Notes

Reaction equation

HRID 351258 reaction equation
[F:1][C:2]([F:18])([F:17])[C:3](=O)[CH2:4][C:5]([C:7]1[CH:12]=[CH:11][C:10]([CH2:13][CH2:14][OH:15])=[CH:9][CH:8]=1)=O.Cl.[N+:20]([C:23]1[CH:28]=[CH:27][C:26]([NH:29][NH2:30])=[CH:25][CH:24]=1)([O-:22])=[O:21].[CH3:31][C:32](O)=[O:33]>O>[C:32]([O:15][CH2:14][CH2:13][C:10]1[CH:11]=[CH:12][C:7]([C:5]2[N:29]([C:26]3[CH:25]=[CH:24][C:23]([N+:20]([O-:22])=[O:21])=[CH:28][CH:27]=3)[N:30]=[C:3]([C:2]([F:18])([F:17])[F:1])[CH:4]=2)=[CH:8][CH:9]=1)(=[O:33])[CH3:31]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 54634014-Nitrophenylhydrazine hydrochlorideHCID 210909544,4,4-Trifluoro-1-[4-(2-hydroxy-ethyl)phenyl]-1,3-butanedione

Product 1

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

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of 4,4,4-trifluoro-1-[4-(2-hydroxy-ethyl)phenyl]-1,3-butanedione (670 mg) and (4-nitrophenyl)hydrazine hydrochloride (439 mg) in AcOH (5 ml) and H2O (0.5 ml) was stirred at ambient temperature overnight. The mixture was concentrated in vacuo, and the residue was partitioned between AcOEt and 1M HCl. The organic layer was washed with 1M HCl for two times, saturated aqueous sodium bicarbonate solution for three times, and saturated aqueous sodium chloride solution, dried over magnesium sulfate, and concentrated in vacuo. The residue was purified by silica gel column chromatography eluted with AcOEt/n-hexane=10% and 15% to give 2-{4-[1-(4-nitrophenyl)-3-(trifluoromethyl)-1H-pyrazol-5-yl]phenyl}ethyl acetate (501 mg) as an oil.

Workup

  1. concentrationThe mixture was concentrated in vacuo
  2. customthe residue was partitioned between AcOEt and 1M HCl
  3. washThe organic layer was washed with 1M HCl for two times, saturated aqueous sodium bicarbonate solution for three times, and saturated aqueous sodium chloride solution
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by silica gel column chromatography
  7. washeluted with AcOEt/n-hexane=10% and 15%

Sources & evidence

ORD record
ord-fe24ce61ef9646d38c28aae168c4e2e5
Source dataset
uspto-grants-2007_02
Patent number
US07183306B2

Reaction notes

Loading…