Sodium sulfate decahydrate → (3-amino-1-phenyl-1H-pyrazol-4-yl)methanol

HRID 2221618Notes

Reaction equation

HRID 2221618 reaction equation
[NH2:1][C:2]1[C:6]([C:7](OCC)=[O:8])=[CH:5][N:4]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[N:3]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-].O.O.O.O.O.O.O.O.O.O.S([O-])([O-])(=O)=O.[Na+].[Na+]>O1CCCC1>[NH2:1][C:2]1[C:6]([CH2:7][OH:8])=[CH:5][N:4]([C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=2)[N:3]=1

Participants

5

Reactant 3

HCID 62649Sodium sulfate decahydrateHCID 14590586Ethyl 3-amino-1-phenyl-1H-pyrazole-4-carboxylateHCID 21226445Aluminium lithium hydride

Product 1

HCID 23076463(3-amino-1-phenyl-1H-pyrazol-4-yl)methanolYield 82%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

A solution (70 mL) of ethyl 3-amino-1-phenyl-1H-pyrazole-4-carboxylate (17.2 g) in tetrahydrofuran was added dropwise to a mixture of lithium aluminum hydride (3.39 g) and tetrahydrofuran (130 mL) on an ice bath. The reaction mixture was heated under reflux for 2 hrs. To this reaction mixture was added sodium sulfate decahydrate by small portions with stirring until foams disappeared on an ice bath, and tetrahydrofuran (50 mL) was further added. After further stirring for 2 hrs., the reaction mixture was filtered, and the filtrate was concentrated. Recrystallization of the residue from tetrahydrofuran-hexane gave (3-amino-1-phenyl-1H-pyrazol-4-yl)methanol as pale-yellow crystals (10.02 g, yield 82%). The crystals were recrystallized from ethyl acetate-hexane. melting point: 127-128° C.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureunder reflux for 2 hrs
  3. customdisappeared on an ice bath
  4. stirringAfter further stirring for 2 hrs
  5. filtration, the reaction mixture was filtered
  6. concentrationthe filtrate was concentrated
  7. customRecrystallization of the residue from tetrahydrofuran-hexane

Sources & evidence

ORD record
ord-fd1f78924e754166923e43ff96612c3f
Source dataset
uspto-grants-2008_05
Patent number
US07368578B2

Reaction notes

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