Triethylamine → 2,4-Dihydro-2-(4-methoxyphenyl)-5-propyl-3H-pyrazol-3-one

HRID 242181Notes

Reaction equation

HRID 242181 reaction equation
O=[C:2]([CH2:9][CH2:10][CH3:11])[CH2:3][C:4](OCC)=[O:5].[CH3:12][O:13][C:14]1[CH:19]=[CH:18][C:17]([NH:20][NH2:21])=[CH:16][CH:15]=1.CCN(CC)CC>CC(O)=O>[CH3:12][O:13][C:14]1[CH:19]=[CH:18][C:17]([N:20]2[C:4](=[O:5])[CH2:3][C:2]([CH2:9][CH2:10][CH3:11])=[N:21]2)=[CH:16][CH:15]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 77023(4-Methoxyphenyl)hydrazineHCID 238498Ethyl 3-oxohexanoate

Product 1

HCID 142312202,4-Dihydro-2-(4-methoxyphenyl)-5-propyl-3H-pyrazol-3-oneYield 59%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
120 °C

Procedure

To a suspension of ethyl 3-oxohexanoate (0.58 mL, 3.62 mmol) and (4-methoxyphenyl)hydrazine (0.50 g, 3.62 mmol) in AcOH (3.5 mL) was added Et3N (0.58 mL, 4.16 mmol). The mixture was stirred at 120° C. for 30 h. The solvent was removed by evaporation, and the residue was dissolved in DCM/EtOAc which was washed with saturated aqueous NaHCO3, followed by water and dried using phase separator. Concentration in vacuo, and purification using silica chromatography (CH2Cl2:Et2O 3:1) gave 1-(4-methoxyphenyl)-3-propyl-1H-pyrazol-5(4H)-one (495 mg, 59%).

Workup

  1. customThe solvent was removed by evaporation
  2. dissolutionthe residue was dissolved in DCM/EtOAc which
  3. washwas washed with saturated aqueous NaHCO3
  4. customdried
  5. concentrationConcentration
  6. customin vacuo, and purification

Sources & evidence

ORD record
ord-00d713c860a54d63aa89c23c58641308
Source dataset
uspto-grants-2014_02
Patent number
US08653112B2

Reaction notes

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