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

HRID 7144

Reaction equation

HRID 7144 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-9b276c372b2c47e7b5b6464e07e242b6
Source dataset
uspto-grants-2006_08
Patent number
US07084155B2

Linked notes

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