(3-amino-1-phenyl-1H-pyrazol-4-yl)methanol → 3-amino-1-phenyl-1H-pyrazole-4-carbaldehyde

HRID 2221619Notes

Reaction equation

HRID 2221619 reaction equation
[NH2:1][C:2]1[C:6]([CH2:7][OH:8])=[CH:5][N:4]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[N:3]=1>[O-2].[O-2].[Mn+4].O1CCCC1>[NH2:1][C:2]1[C:6]([CH:7]=[O:8])=[CH:5][N:4]([C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=2)[N:3]=1

Participants

4

Reactant 1

HCID 23076463(3-amino-1-phenyl-1H-pyrazol-4-yl)methanol

Product 1

HCID 230766113-amino-1-phenyl-1H-pyrazole-4-carbaldehydeYield 82.4%

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of (3-amino-1-phenyl-1H-pyrazol-4-yl)methanol (12.29 g), activated manganese dioxide (35 g) and tetrahydrofuran (200 mL) was stirred at room temperature for 16 hrs. The reaction mixture was filtered, and the filtrate was concentrated. Recrystallization of the residue from tetrahydrofuran-hexane gave 3-amino-1-phenyl-1H-pyrazole-4-carbaldehyde as pale-yellow crystals (10.02 g, yield 82%). melting point: 129-130° C.

Workup

  1. filtrationThe reaction mixture was filtered
  2. concentrationthe filtrate was concentrated
  3. customRecrystallization of the residue from tetrahydrofuran-hexane

Sources & evidence

ORD record
ord-beb7c6aaacdc48baa96767af1f113749
Source dataset
uspto-grants-2008_05
Patent number
US07368578B2

Reaction notes

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