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

HRID 1170906Notes

Reaction equation

HRID 1170906 reaction equation
[CH3:1][C:2]1[C:7]([CH2:8][OH:9])=[CH:6][CH:5]=[CH:4][N:3]=1>ClCCl.[O-2].[Mn+2]>[CH3:1][C:2]1[N:3]=[CH:4][CH:5]=[CH:6][C:7]=1[CH:8]=[O:9]

Participants

4

Reactant 1

HCID 302564(2-Methylpyridin-3-yl)methanol

Product 1

HCID 110838812-Methylpyridine-3-carbaldehydeYield 69.1%

Reagents, catalysts & solvents 2

HCID 160959Manganese oxideCatalystHCID 6344DichloromethaneSolvent

Procedure

A mixture of (2-methylpyridin-3-yl)methanol (1.0 g, 8.12 mmol) in dichloromethane (10 mL) and manganese oxide (7.06 g, 81.2 mmol) was stirred at room temperature for sixty hours and then heated at 45° C. for 4 h. The reaction was filtered through celite and a plug of silica gel (5×7 cm) using ethyl acetate as eluent. The filtrate was then concentrated to give 2-methyl nicotinaldehyde as an oil (680 mg). 1H NMR (400 MHz, CDCl3) δ 10.32 (s, 1H), 8.67 (dd, 1H), 8.09 (dd, 1H), 7.31 (dd, 1H), 2.88 (s, 3H).

Workup

  1. temperatureheated at 45° C. for 4 h
  2. filtrationThe reaction was filtered through celite
  3. concentrationThe filtrate was then concentrated

Sources & evidence

ORD record
ord-a8ec2e8add184d8ca14b744b49bfe891
Source dataset
uspto-grants-2010_11
Patent number
US07829572B2

Reaction notes

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