[5-(3-chloro-benzylamino)-2-methyl-2H-pyrazol-3-yl]-methanol → 5-(3-chloro-benzylamino)-2-methyl-2H-pyrazole-3-carbaldehyde

HRID 1024321Notes

Reaction equation

HRID 1024321 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:15]=[CH:16][CH:17]=1)[CH2:5][NH:6][C:7]1[CH:8]=[C:9]([CH2:13][OH:14])[N:10]([CH3:12])[N:11]=1>[O-2].[Mn+4].[O-2].ClCCl>[Cl:1][C:2]1[CH:3]=[C:4]([CH:15]=[CH:16][CH:17]=1)[CH2:5][NH:6][C:7]1[CH:8]=[C:9]([CH:13]=[O:14])[N:10]([CH3:12])[N:11]=1

Participants

4

Reactant 1

HCID 57619232[5-(3-chloro-benzylamino)-2-methyl-2H-pyrazol-3-yl]-methanol

Product 1

HCID 576191725-(3-chloro-benzylamino)-2-methyl-2H-pyrazole-3-carbaldehydeYield 60%

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 6344DichloromethaneSolvent

Procedure

[5-(3-Chloro-benzylamino)-2-methyl-2H-pyrazol-3-yl]-methanol (647, 0.821 g, 3.26 mmol) was combined with dichloromethane (70 mL) and manganese(IV) oxide (4 g). The reaction was stirred at room temperature overnight under an atmosphere of nitrogen. The mixture was filtered through Celite and concentrated. Purification by silica gel column chromatography eluting with a gradient of ethyl acetate (10-100%) in hexane gave the desired aldehyde (648, 0.482 g, 60%).

Workup

  1. filtrationThe mixture was filtered through Celite
  2. concentrationconcentrated
  3. customPurification by silica gel column chromatography
  4. washeluting with a gradient of ethyl acetate (10-100%) in hexane

Sources & evidence

ORD record
ord-f6ba7a0e5bb74457821a898bdd4fe9b5
Source dataset
uspto-grants-2014_05
Patent number
US08722702B2

Reaction notes

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