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

HRID 2274974Notes

Reaction equation

HRID 2274974 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)
  4. dry with materialThe combined organic extracts were dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-4acac7276a8a47d58d29aa45aab0cef8
Source dataset
uspto-grants-2015_09
Patent number
US09126999B2

Reaction notes

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