Methyl 6-(hydroxymethyl)picolinate → Methyl 6-formylpyridine-2-carboxylate

HRID 1174156Notes

Reaction equation

HRID 1174156 reaction equation
[OH:1][CH2:2][C:3]1[N:8]=[C:7]([C:9]([O:11][CH3:12])=[O:10])[CH:6]=[CH:5][CH:4]=1>ClCCl.[O-2].[O-2].[Mn+4]>[CH:2]([C:3]1[N:8]=[C:7]([C:9]([O:11][CH3:12])=[O:10])[CH:6]=[CH:5][CH:4]=1)=[O:1]

Participants

4

Reactant 1

HCID 11513809Methyl 6-(hydroxymethyl)picolinate

Product 1

HCID 12575850Methyl 6-formylpyridine-2-carboxylateYield 87%

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 6344DichloromethaneSolvent

Conditions

Temperature
25 °C

Procedure

A solution of the product from Example 17A (8 g, 48 mmol) in dichloromethane (200 mL) was treated with electrolytic manganese dioxide (41.67 g, 0.48 mol). The mixture was stirred for 4 days at 25° C. and filtered through celite. The filtrate was concentrated under reduced pressure and the residue was purified by chromatography on silica gel eluting with 5% methanol in dichloromethane to give the title compound as a white solid (6.9 g, 87% yield).

Workup

  1. filtrationfiltered through celite
  2. concentrationThe filtrate was concentrated under reduced pressure
  3. customthe residue was purified by chromatography on silica gel eluting with 5% methanol in dichloromethane

Sources & evidence

ORD record
ord-4f1616cc4ab249bca1c6bed508f50207
Source dataset
uspto-grants-2010_11
Patent number
US07834043B2

Reaction notes

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