Ethyl Acetoacetate → HCID 178428853, compound

HRID 497956Notes

Reaction equation

HRID 497956 reaction equation
[CH3:1][C:2]1[CH:6]=[C:5]([NH2:7])[N:4]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][N:9]=2)[N:3]=1.[C:14](OCC)(=[O:19])[CH2:15][C:16]([CH3:18])=O.[OH-].[Na+]>O>[CH3:1][C:2]1[C:6]2[C:14]([OH:19])=[CH:15][C:16]([CH3:18])=[N:7][C:5]=2[N:4]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][N:9]=2)[N:3]=1

Participants

5

Reactant 3

HCID 8868Ethyl AcetoacetateHCID 14798Sodium HydroxideHCID 7351323-Methyl-1-(pyridin-2-yl)-1H-pyrazol-5-amine

Product 1

HCID 178428853HCID 178428853, compoundYield 30%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
130 °C

Procedure

A mixture of 3-methyl-1-(2-pyridinyl)-1H-pyrazol-5-amine (1.8 g, 10 mmol) and polyphosphoric acid (4.2 g) was heated at 130° C. The mixture was stirred thoroughly at the same temperature, while ethyl acetoacetate (1.3 mL, 10 mmol) was added dropwise thereto, and the resulting mixture was stirred at the same temperature for 1 hour. The mixture was cooled to room temperature, iced water was added thereto. The mixture was neutralized with an aqueous sodium hydroxide solution, and organic matter was extracted with chloroform. The extract was washed with saturated brine and dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The residue thus obtained was purified by silica gel column chromatography (chloroform:methanol=50:1 to 20:1), and recrystallized from ethyl acetate to give the title compound (0.72 g, 30% yield).

Workup

  1. additionwas added dropwise
  2. temperatureThe mixture was cooled to room temperature
  3. extractionwas extracted with chloroform
  4. washThe extract was washed with saturated brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. customthe solvent was evaporated under reduced pressure
  7. customThe residue thus obtained
  8. customwas purified by silica gel column chromatography (chloroform:methanol=50:1 to 20:1)
  9. customrecrystallized from ethyl acetate

Sources & evidence

ORD record
ord-c4b555246834477ea48950c22b63e512
Source dataset
uspto-grants-2005_09
Patent number
US06949648B2

Reaction notes

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