Hydrochloric Acid → 1-(1,3-dimethyl-1H-pyrazol-4-yl)ethan-1-one

HRID 62220

Reaction equation

HRID 62220 reaction equation
[CH3:1][N:2]([CH:7]=[C:8]([C:12](=[O:14])[CH3:13])[C:9](=O)[CH3:10])[N:3]=C(C)C.Cl>C(O)C.O>[CH3:1][N:2]1[CH:7]=[C:8]([C:12](=[O:14])[CH3:13])[C:9]([CH3:10])=[N:3]1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 236352723-((1-Methyl-2-(propan-2-ylidene)hydrazinyl)methylene)pentane-2,4-dione

Product 1

HCID 8439771-(1,3-dimethyl-1H-pyrazol-4-yl)ethan-1-one

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

3-((1-methyl-2-(propan-2-ylidene)hydrazinyl)methylene)pentane-2,4-dione (Preparation 3, 9.1 g) was dissolved in Ethanol (20 mL) and treated with 1M Hydrogen chloride in Water (20 mL), the reaction solution was stirred at room temperature for 15 minutes. The reaction solution was then concentrated under vacuum with a rotavap to approximately 20 mL total volume. The reaction solution was then treated with saturated aqueous sodium bicarbonate (45 mL), and extracted with methylene chloride (4×50 mL) The combined organic extracts were dried over sodium sulfate, filtered and concentrated in vacuo afford the title compound as a light orange solid. (6.2 g, 97%).

Workup

  1. concentrationThe reaction solution was then concentrated under vacuum with a rotavap to approximately 20 mL total volume
  2. additionThe reaction solution was then treated with saturated aqueous sodium bicarbonate (45 mL)
  3. extractionextracted with methylene chloride (4×50 mL) The combined organic extracts
  4. dry with materialwere dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-985c132fa4894d0b82cf4737d412a941
Source dataset
uspto-grants-2016_09
Patent number
US09446046B2

Linked notes

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