(6-Chloro-5-methylpyridin-3-yl)methanol → 6-Chloro-5-methylpyridine-3-carbaldehyde

HRID 420752

Reaction equation

HRID 420752 reaction equation
[Cl:1][C:2]1[N:7]=[CH:6][C:5]([CH2:8][OH:9])=[CH:4][C:3]=1[CH3:10]>C(Cl)Cl>[Cl:1][C:2]1[N:7]=[CH:6][C:5]([CH:8]=[O:9])=[CH:4][C:3]=1[CH3:10]

Participants

3

Reactant 1

HCID 11686949(6-Chloro-5-methylpyridin-3-yl)methanol

Product 1

HCID 197106816-Chloro-5-methylpyridine-3-carbaldehydeYield 69.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
40 °C

Procedure

A mixture of (6-chloro-5-methyl-3-pyridinyl)methanol (300 mg, 1.904 mmol), CrO2 (Magtrieve) (2.398 g, 28.5 mmol), and DCM (15 ml) was stirred at 40° C. in a closed tube overnight. TLC showed some starting material remaining. Additional CrO2 (0.8 g) was added. After heating 4 additional hours, TLC showed full conversion. Filtration and concentration afforded 6-chloro-5-methyl-3-pyridinecarbaldehyde (204.8 mg, 69%) as a white solid.

Workup

  1. temperatureAfter heating 4 additional hours, TLC
  2. filtrationFiltration and concentration

Sources & evidence

ORD record
ord-a96b34040b734cec8923f0d39fc8cb8d
Source dataset
uspto-grants-2012_01
Patent number
US08097628B2

Linked notes

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