(3-Methylpyridin-2-yl)methanol → 3-Methylpyridine-2-carboxaldehyde

HRID 747342

Reaction equation

HRID 747342 reaction equation
[OH:1][CH2:2][C:3]1[C:8]([CH3:9])=[CH:7][CH:6]=[CH:5][N:4]=1>C(Cl)Cl.O=[Mn]=O>[CH3:9][C:8]1[C:3]([CH:2]=[O:1])=[N:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 1

HCID 1514369(3-Methylpyridin-2-yl)methanol

Product 1

HCID 15018743-Methylpyridine-2-carboxaldehydeYield 64%

Reagents, catalysts & solvents 2

HCID 14801Manganese dioxideCatalystHCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 2-(hydroxymethyl)-3-methylpyridine (1.08 g, 8.77 mmol) in dry CH2Cl2 (45 mL) at room temperature was added MnO2 (8.09 g, 79.1 mmol). The mixture was stirred for 21 hrs then filtered through celite. The filtrate was concentrated to give 0.68 g (64%) of 3-methylpyridine-2-carboxaldehyde. 1H NMR (CDCl3) □ 2.66 (s, 3H), 7.39 (dd, 1H, J=8.3, 4.3 Hz), 7.63 (d, 1H, J=7.9 Hz), 8.66 (d, 1H, J=3.3 Hz), 10.19 (s, 1H). This was used without further purification.

Workup

  1. filtrationthen filtered through celite
  2. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-79276cd25702424f90854d58f89435ed
Source dataset
uspto-grants-2008_07
Patent number
US07396840B2

Linked notes

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