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

HRID 923361Notes

Reaction equation

HRID 923361 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-2,3-pyridinedicarboxylic acid anhydride were dissolved in 165 g (5.16 mol) methanol at room temperature, causing formation of monoesters. 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 hrs at 65° C.

Workup

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

Sources & evidence

ORD record
ord-c57cf6fd58c74b67bf71faf6a85ee8d8
Source dataset
uspto-grants-2016_03
Patent number
US09278977B2

Reaction notes

Loading…