(2-Ethyl-6-methyl-pyridin-4-yl)-methanol → 2-Ethyl-6-methylisonicotinaldehyde

HRID 2366120Notes

Reaction equation

HRID 2366120 reaction equation
[CH2:1]([C:3]1[CH:8]=[C:7]([CH2:9][OH:10])[CH:6]=[C:5]([CH3:11])[N:4]=1)[CH3:2]>C(Cl)Cl.O=[Mn]=O>[CH2:1]([C:3]1[CH:8]=[C:7]([CH:9]=[O:10])[CH:6]=[C:5]([CH3:11])[N:4]=1)[CH3:2]

Participants

4

Reactant 1

HCID 67520483(2-Ethyl-6-methyl-pyridin-4-yl)-methanol

Product 1

HCID 729421392-Ethyl-6-methylisonicotinaldehydeYield 107.2%

Reagents, catalysts & solvents 2

HCID 14801Manganese dioxideCatalystHCID 6344DichloromethaneSolvent

Procedure

A solution of crude (2-ethyl-6-methyl-pyridin-4-yl)-methanol (453.6 mg, 3 mmol) in DCM (30 mL) and MnO2 (2.6 g, 30 mmol) is added. The mixture is stirred at rt for 15 h, filtered and evaporated (130 mbar, 45° C.) to give crude 2-ethyl-6-methyl-pyridine-4-carbaldehyde (0.48 g); 1H NMR (CDCl3): δ 10.02 (s, 1 H), 7.37 (s, 2 H), 2.89 (q, J=7.6 Hz, 2 H), 2.64 (s, 3 H), 1.33 (t, J=7.6 Hz, 3 H).

Workup

  1. filtrationfiltered
  2. customevaporated (130 mbar, 45° C.)

Sources & evidence

ORD record
ord-c62fc32990ec4ac28a9a543cbcb8bd3c
Source dataset
uspto-grants-2014_04
Patent number
US08697732B2

Reaction notes

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