Sodium Carbonate → 3-(1-Methyl-1H-pyrazol-3-yl)aniline

HRID 2101673Notes

Reaction equation

HRID 2101673 reaction equation
Br[C:2]1[C:3]([C:8]2[CH:9]=[C:10]([CH:12]=[CH:13][CH:14]=2)[NH2:11])=[N:4][N:5]([CH3:7])[CH:6]=1.C(=O)([O-])[O-].[Na+].[Na+]>C(O)C.[Pd]>[CH3:7][N:5]1[CH:6]=[CH:2][C:3]([C:8]2[CH:9]=[C:10]([CH:12]=[CH:13][CH:14]=2)[NH2:11])=[N:4]1

Participants

5

Reactant 2

HCID 10340Sodium CarbonateHCID 27353913-(4-Bromo-1-Methyl-1H-Pyrazol-3-Yl)Aniline

Product 1

HCID 27353963-(1-Methyl-1H-pyrazol-3-yl)anilineYield 72.8%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent2×

Procedure

A solution of 3-(4-bromo-1-methyl-1H-pyrazol-3-yl)aniline (1.0 g) (available from Maybridge) in ethanol (20 ml) was added to a pre-hydrogenated suspension of 5% palladium on charcoal (0.5 g) in ethanol (40 ml). The resulting suspension was stirred under an atmosphere of hydrogen for 3 h. The mixture was filtered through ‘hyflo’ filter aid and the filter pad washed with ethanol (50 ml). The combined filtrate was evaporated in vacuo to give a brown gum. This gum was treated with 2M sodium carbonate solution (100 ml) and extracted with ethyl acetate (2×100 ml); the organic layer was dried over magnesium sulphate and the solvent removed in vacuo. Purification by chromatography on silica gel, eluting with diethyl ether, gave the title compound as a white crystalline solid (0.5 g).

Workup

  1. filtrationThe mixture was filtered through ‘hyflo’
  2. filtrationfilter aid
  3. washthe filter pad washed with ethanol (50 ml)
  4. customThe combined filtrate was evaporated in vacuo
  5. customto give a brown gum
  6. extractionextracted with ethyl acetate (2×100 ml)
  7. dry with materialthe organic layer was dried over magnesium sulphate
  8. customthe solvent removed in vacuo
  9. customPurification by chromatography on silica gel
  10. washeluting with diethyl ether

Sources & evidence

ORD record
ord-155c8276c98647aa9db96d47b4ae47be
Source dataset
uspto-grants-2009_08
Patent number
US07572915B2

Reaction notes

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