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

HRID 509242Notes

Reaction equation

HRID 509242 reaction equation
[CH3:1][O:2][CH2:3][C:4]1[CH:5]=[C:6]([C:14]([O:16]C)=[O:15])[C:7]([C:10]([O:12]C)=[O:11])=[N:8][CH:9]=1.[OH-].[Na+]>O>[CH3:1][O:2][CH2:3][C:4]1[CH:5]=[C:6]([C:14]([OH:16])=[O:15])[C:7]([C:10]([OH:12])=[O:11])=[N:8][CH:9]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 110966932,3-Pyridinedicarboxylic acid, 5-(methoxymethyl)-, dimethyl ester

Product 1

HCID 109983115-(Methoxymethyl)pyridine-2,3-dicarboxylic acidYield 83.9%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of dimethyl 5-(methoxymethyl)-2,3-pyridinedicarboxylate (60.0 g, 0.25 mol) and 50% sodium hydroxide solution (50.0 g, 0.63 mol) in water is heated at 90-110° C. for 2 hours under nitrogen while distilling off methanol and water. The reaction mixture is cooled to 10° C., treated with sulfuric acid to adjust the pH to 2.0 and filtered to obtain a solid. The solid is washed with water and vacuum dried to give the title product as a white solid (44.3 g, mp 161-162° C.).

Workup

  1. distillationwhile distilling off methanol and water
  2. temperatureThe reaction mixture is cooled to 10° C.
  3. additiontreated with sulfuric acid
  4. filtrationfiltered
  5. customto obtain a solid
  6. washThe solid is washed with water and vacuum
  7. customdried

Sources & evidence

ORD record
ord-2f483b3b67d3498bb722df2b7e573410
Source dataset
uspto-grants-2015_08
Patent number
US09096570B2

Reaction notes

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