Water → Methyl 6-formylpyridine-2-carboxylate

HRID 376298

Reaction equation

HRID 376298 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([CH2:11][OH:12])[N:6]=1)=[O:4].O>ClCCCl.[O-2].[O-2].[Mn+4]>[CH3:1][O:2][C:3]([C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([CH:11]=[O:12])[N:6]=1)=[O:4]

Participants

5

Reactant 2

HCID 962WaterHCID 11513809Methyl 6-(hydroxymethyl)picolinate

Product 1

HCID 12575850Methyl 6-formylpyridine-2-carboxylateYield 79%

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 111,2-DichloroethaneSolvent

Procedure

A solution of 3 g of 6-hydroxymethylpyridine-2-carboxylic acid methyl ester (16.5 mmol) in 70 ml of 1,2-dichloroethane containing 15 g of manganese dioxide (165 mmol) is heated under reflux for 4 hours with removal of the water formed continuously. The solid is removed by filtration on celite and then the dichloromethane is evaporated off. The title product is isolated by chromatography on a silica column (eluent: dichloromethane/ethyl acetate; 70:30). 2.33 g of a yellow oil are recovered.

Workup

  1. customformed continuously
  2. customThe solid is removed by filtration on celite
  3. customthe dichloromethane is evaporated off

Sources & evidence

ORD record
ord-7eeb93095125479cbb6978ebce1004e3
Source dataset
uspto-grants-2000_02
Patent number
US06020345

Linked notes

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