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Hydrochloric Acid → 2-(3-Ethyl-indan-5-yl)-5-methyl-2,4-dihydro-pyrazol-3-one

HRID 384375
Notes
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Reaction equation

HRID 384375 reaction equation
[CH2:1]([CH:3]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([N:12](C(OC(C)(C)C)=O)[NH:13]C(OC(C)(C)C)=O)[CH:10]=2)[CH2:5][CH2:4]1)[CH3:2].C(O[C:31](=[O:36])[CH2:32][C:33](=O)[CH3:34])C.Cl>C(O)C.O>[CH2:1]([CH:3]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([N:12]3[C:31](=[O:36])[CH2:32][C:33]([CH3:34])=[N:13]3)[CH:10]=2)[CH2:5][CH2:4]1)[CH3:2]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 8868Ethyl AcetoacetateHCID 57483834di-tert-butyl 1-(3-ethyl-2,3-dihydro-1H-inden-5-yl)hydrazine-1,2-dicarboxylate

Product 1

HCID 574837832-(3-Ethyl-indan-5-yl)-5-methyl-2,4-dihydro-pyrazol-3-oneYield 39.8%

Reagents, catalysts & solvents 1

HCID 19096565Water ethanol
Solvent

Procedure

Di-tert-butyl 1-(3-ethyl-2,3-dihydro-1H-inden-5-yl)hydrazine-1,2-dicarboxylate 41c (3.43 g, 9.1 mmol) was dissolved in 50 mL of a solvent mixture of ethanol/water (V:V=3:2) followed by addition of 3-oxo-butanoic acid ethyl ester (1.18 g, 9.1 mmol) and 4.55 mL of hydrochloric acid (6 N). Upon completion of the addition, the reaction mixture was heated to reflux and reacted for 1 hour. The reaction was monitored by TLC until the disappearance of the starting materials. The mixture was concentrated under reduced pressure to remove ethanol and then extracted with dichloromethane (15 mL×3). The combined organic extracts were dried over anhydrous sodium sulfate, filtered to remove the drying agent and concentrated under reduced pressure. The residue was purified by silica gel column chromatography to obtain the title compound 2-(3-ethyl-indan-5-yl)-5-methyl-2,4-dihydro-pyrazol-3-one 41d (0.712 g, 39.8%) as a yellow oil.

Workup

  1. additionUpon completion of the addition
  2. temperaturethe reaction mixture was heated
  3. temperatureto reflux
  4. customreacted for 1 hour
  5. concentrationThe mixture was concentrated under reduced pressure
  6. customto remove ethanol
  7. extractionextracted with dichloromethane (15 mL×3)
  8. dry with materialThe combined organic extracts were dried over anhydrous sodium sulfate
  9. filtrationfiltered
  10. customto remove the drying agent
  11. concentrationconcentrated under reduced pressure
  12. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-19e8ae138afe409aabf4c3d50b772909
Source dataset
uspto-grants-2013_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08367710B2

Reaction notes

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