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

HRID 384289Notes

Reaction equation

HRID 384289 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 and the reaction was monitored by TLC until the disappearance of the starting materials. 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-9e018d116e9341f7801e9463fc0d14f8
Source dataset
uspto-grants-2013_02
Patent number
US08367710B2

Reaction notes

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