Methanol → 2-Hydroxy-6-methylpyridine-3-carbaldehyde

HRID 657161Notes

Reaction equation

HRID 657161 reaction equation
[OH:1][CH2:2][C:3]1[C:4](=[O:10])[NH:5][C:6]([CH3:9])=[CH:7][CH:8]=1.C1COCC1.CO>C(Cl)Cl.O=[Mn]=O>[CH3:9][C:6]1[NH:5][C:4](=[O:10])[C:3]([CH:2]=[O:1])=[CH:8][CH:7]=1

Participants

6

Reactant 3

HCID 887MethanolHCID 8028TetrahydrofuranHCID 202160783-(Hydroxymethyl)-6-methylpyridin-2(1H)-one

Product 1

HCID 127224622-Hydroxy-6-methylpyridine-3-carbaldehydeYield 101%

Reagents, catalysts & solvents 2

HCID 14801Manganese dioxideCatalystHCID 6344DichloromethaneSolvent

Conditions

Temperature
57 °C

Procedure

3-(hydroxymethyl)-6-methyl-2(1H)-pyridinone (2.0 g, 13 mmol) was dissolved in CH2Cl2(80 mL), THF (80 mL) and MeOH (5 mL), MnO2 (3.7 g, 43 mmol) was added. The reaction mixture was heated at 57° C. for 18 hours. The reaction was filtered through a pad of Celite® and concentrated to give a solid (1.8 g, 90%). LCMS (ES+) m/z 138 (MH+).

Workup

  1. filtrationThe reaction was filtered through a pad of Celite®
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-38e5c289d77b47e98b517c9b86820670
Source dataset
uspto-grants-2011_12
Patent number
US08071592B2

Reaction notes

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