[6-(1H-pyrazol-1-yl)pyridin-2-yl]methanol → 6-(1H-Pyrazol-1-yl)-2-pyridinecarboxaldehyde

HRID 594258Notes

Reaction equation

HRID 594258 reaction equation
[N:1]1([C:6]2[N:11]=[C:10]([CH2:12][OH:13])[CH:9]=[CH:8][CH:7]=2)[CH:5]=[CH:4][CH:3]=[N:2]1>ClCCCl.O=[Mn]=O>[N:1]1([C:6]2[N:11]=[C:10]([CH:12]=[O:13])[CH:9]=[CH:8][CH:7]=2)[CH:5]=[CH:4][CH:3]=[N:2]1

Participants

4

Reactant 1

HCID 62255710[6-(1H-pyrazol-1-yl)pyridin-2-yl]methanol

Product 1

HCID 105114076-(1H-Pyrazol-1-yl)-2-pyridinecarboxaldehyde

Reagents, catalysts & solvents 2

HCID 14801Manganese dioxideCatalystHCID 111,2-DichloroethaneSolvent

Procedure

A solution of (6-(1H-pyrazol-1-yl)pyridin-2-yl)methanol (295 mg; 1.68 mmol) in anh. DCE (6 ml) was treated with MnO2 (1.174 g; 13.51 mmol), and the resulting mixture was stirred at reflux, under nitrogen, for 2 h. After cooling to rt, the resulting reaction mixture was filtered over celite, and the separated solids were washed with DCM. The filtrate was concentrated to dryness under reduced pressure giving 6-(1H-pyrazol-1-yl)picolinaldehyde as an off-white solid. LC-MS (conditions C): tR=0.74 min.; [M+H]+: 173.88 g/mol.

Workup

  1. temperatureat reflux, under nitrogen, for 2 h
  2. customthe resulting reaction mixture
  3. filtrationwas filtered over celite
  4. washthe separated solids were washed with DCM
  5. concentrationThe filtrate was concentrated to dryness under reduced pressure

Sources & evidence

ORD record
ord-bb17d829b40c4c1aad155d4dff028fb0
Source dataset
uspto-grants-2016_01
Patent number
US09242970B2

Reaction notes

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