Sodium sulfate decahydrate → [3-(methylamino)-1-phenyl-1H-pyrazol-4-yl]methanol

HRID 2221653Notes

Reaction equation

HRID 2221653 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH:7]([NH:9][C:10]1[C:14]([C:15](OCC)=[O:16])=[CH:13][N:12]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[N:11]=1)=O.O.O.O.O.O.O.O.O.O.O.S([O-])([O-])(=O)=O.[Na+].[Na+]>O1CCCC1>[CH3:7][NH:9][C:10]1[C:14]([CH2:15][OH:16])=[CH:13][N:12]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[N:11]=1

Participants

5

Reactant 3

HCID 62649Sodium sulfate decahydrateHCID 21226445Aluminium lithium hydrideHCID 23076448ethyl 3-(formylamino)-1-phenyl-1H-pyrazole-4-carboxylate

Product 1

HCID 69217492[3-(methylamino)-1-phenyl-1H-pyrazol-4-yl]methanolYield 96%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

Lithium aluminum hydride (7.50 g) was added to tetrahydrofuran (200 mL) under ice-cooling. To the obtained mixture was added dropwise a solution (100 mL) of ethyl 3-(formylamino)-1-phenyl-1H-pyrazole-4-carboxylate (20.50 g) in tetrahydrofuran, and the mixture was heated under reflux for 1.5 hrs. To the obtained mixture was added small portions of sodium sulfate decahydrate (50 g) on an ice bath, and the mixture was stirred for 2 hrs. while adding tetrahydrofuran (50 mL) as appropriate to allow stirring. Solids were filtered off and the filtrate was concentrated to give [3-(methylamino)-1-phenyl-1H-pyrazol-4-yl]methanol as a colorless oil (15.42 g, yield 96%).

Workup

  1. temperaturecooling
  2. temperaturethe mixture was heated
  3. temperatureunder reflux for 1.5 hrs
  4. stirringto allow stirring
  5. filtrationSolids were filtered off
  6. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-e787ff7a19494444a9d55a1cf4656842
Source dataset
uspto-grants-2008_05
Patent number
US07368578B2

Reaction notes

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