[3-(methylamino)-1-phenyl-1H-pyrazol-4-yl]methanol → 3-(methylamino)-1-phenyl-1H-pyrazole-4-carbaldehyde

HRID 2221654Notes

Reaction equation

HRID 2221654 reaction equation
[CH3:1][NH:2][C:3]1[C:7]([CH2:8][OH:9])=[CH:6][N:5]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[N:4]=1>[O-2].[O-2].[Mn+4].O1CCCC1>[CH3:1][NH:2][C:3]1[C:7]([CH:8]=[O:9])=[CH:6][N:5]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[N:4]=1

Participants

4

Reactant 1

HCID 69217492[3-(methylamino)-1-phenyl-1H-pyrazol-4-yl]methanol

Product 1

HCID 230763643-(methylamino)-1-phenyl-1H-pyrazole-4-carbaldehyde

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of [3-(methylamino)-1-phenyl-1H-pyrazol-4-yl]methanol (15.42 g), activated manganese dioxide (50 g) and tetrahydrofuran (150 mL) was stirred at room temperature for 16 hrs. The obtained mixture was filtered, and the filtrate was concentrated. The residue was subjected to silica gel column chromatography to give 3-(methylamino)-1-phenyl-1H-pyrazole-4-carbaldehyde as colorless crystals from a fraction eluted with ethyl acetate-hexane (1:4, v/v). Recrystallization from ethyl acetate-hexane gave colorless needle crystal (9.17 g, yield 60%). melting point: 83-84° C.

Workup

  1. filtrationThe obtained mixture was filtered
  2. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-d9459743dd9e4c50905fa4a369406992
Source dataset
uspto-grants-2008_05
Patent number
US07368578B2

Reaction notes

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