Ethyl Acetoacetate → 2-Indan-5-yl-5-methyl-2,4-dihydro-pyrazol-3-one

HRID 238698Notes

Reaction equation

HRID 238698 reaction equation
[CH2:1]1[C:9]2[C:4](=[CH:5][C:6]([NH:10][NH2:11])=[CH:7][CH:8]=2)[CH2:3][CH2:2]1.[C:12](OCC)(=[O:17])[CH2:13][C:14]([CH3:16])=O>C(O)(=O)C>[CH2:1]1[C:9]2[C:4](=[CH:5][C:6]([N:10]3[C:12](=[O:17])[CH2:13][C:14]([CH3:16])=[N:11]3)=[CH:7][CH:8]=2)[CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 8868Ethyl AcetoacetateHCID 217018272,3-Dihydro-1H-inden-5-ylhydrazine

Product 1

HCID 574837802-Indan-5-yl-5-methyl-2,4-dihydro-pyrazol-3-oneYield 62.3%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
100 °C

Procedure

Indan-5-yl-hydrazine 1h (2.05 g, 13.8 mmol) was dissolved in 50 mL of acetic acid followed by addition of ethyl acetoacetate (1.76 mL, 13.8 mmol). The reaction mixture was heated at 100° C. overnight. The mixture was concentrated under reduced pressure and the resulting residue was purified by silica gel column chromatography to obtain the title compound 2-indan-5-yl-5-methyl-2,4-dihydro-pyrazol-3-one 1i (1.84 g, yield 62.3%) as a yellow solid.

Workup

  1. concentrationThe mixture was concentrated under reduced pressure
  2. customthe resulting residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-37f813e148ab43efbb91c401ef3a6652
Source dataset
uspto-grants-2014_02
Patent number
US08642637B2

Reaction notes

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