Triethylamine → 1-(4-Tolyl)-3-(4-nitrophenyl)-5-aminopyrazole

HRID 1860515Notes

Reaction equation

HRID 1860515 reaction equation
[C:1]([CH2:3][C:4]([C:6]1[CH:11]=[CH:10][C:9]([N+:12]([O-:14])=[O:13])=[CH:8][CH:7]=1)=O)#[N:2].[C:15]1(C)[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[NH:21][NH2:22].[CH2:24](N(CC)CC)C.CCOC(C)=O>C(O)C>[C:19]1([CH3:24])[CH:20]=[CH:15][C:16]([N:21]2[C:1]([NH2:2])=[CH:3][C:4]([C:6]3[CH:11]=[CH:10][C:9]([N+:12]([O-:14])=[O:13])=[CH:8][CH:7]=3)=[N:22]2)=[CH:17][CH:18]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 68256o-TolylhydrazineHCID 5914593-(4-Nitrophenyl)-3-oxopropanenitrile

Product 1

HCID 120186771-(4-Tolyl)-3-(4-nitrophenyl)-5-aminopyrazole

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 2-cyano-4′nitroacetophenone in ethanol (100 mL) at room temperature was added tolylhydrazine (6.44 g, 0.04 mol) and triethylamine (15.4 mL, 0.11 mol). The resulting solution was heated to reflux and maintained at reflux for 1 h. The solution was cooled to room temperature at which time EtOAc (500 mL) was added. The organic solution was washed with brine (2×500 mL), dried over Na2SO4 and concentrated by rotary evaporation. The residue was purified by column chromatography on silica gel eluting with 1:1 hexane/EtOAc to yield 1-(4-tolyl)-3-(4-nitrophenyl)-5-aminopyrazole as a solid.

Workup

  1. temperatureThe resulting solution was heated
  2. temperatureto reflux
  3. temperaturemaintained
  4. temperatureat reflux for 1 h
  5. additionwas added
  6. washThe organic solution was washed with brine (2×500 mL)
  7. dry with materialdried over Na2SO4
  8. concentrationconcentrated by rotary evaporation
  9. customThe residue was purified by column chromatography on silica gel eluting with 1:1 hexane/EtOAc

Sources & evidence

ORD record
ord-4da161b0cc6e4e3dbfe5cadb98633822
Source dataset
uspto-grants-2003_03
Patent number
US06531478B2

Reaction notes

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