Methanol → 5-(Methoxymethyl)pyridine-2,3-dicarboxylic acid

HRID 470375Notes

Reaction equation

HRID 470375 reaction equation
Cl[CH2:2][C:3]1[CH:4]=[C:5]2[C:12](=[O:13])[O:11][C:9](=[O:10])[C:6]2=[N:7][CH:8]=1.[CH3:14][OH:15].[OH-:16].[Na+]>>[CH3:14][O:15][CH2:2][C:3]1[CH:4]=[C:5]([C:12]([OH:11])=[O:13])[C:6]([C:9]([OH:16])=[O:10])=[N:7][CH:8]=1

Participants

4

Reactant 3

HCID 887MethanolHCID 14798Sodium HydroxideHCID 46899675HCID 46899675, compound

Product 1

HCID 109983115-(Methoxymethyl)pyridine-2,3-dicarboxylic acid

Procedure

7.0 g (35 mmol) 5-chloromethyl-pyridine-2,3-dicarboxylic acid anhydride (Va) were dissolved in 165 g (5.16 mol) methanol at room temperature, causing formation of mono-esters. 14 g (350 mmol) NaOH (50% in water) were slowly added whereupon the temperature rose to 50° C. and carboxylate started to precipitate. Stirring was continued for additional 5 h at 65° C.

Workup

  1. customrose to 50° C.
  2. customto precipitate

Sources & evidence

ORD record
ord-474c3534e761469691a089eb2380848e
Source dataset
uspto-grants-2014_01
Patent number
US08629279B2

Reaction notes

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