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

HRID 1078085
Notes
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Reaction equation

HRID 1078085 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
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

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
10 °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. temperatureis heated at 90°-110° C. for 2 hours under nitrogen
  2. distillationwhile distilling off methanol and water
  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-6f0ec720883847bc9a4ef99ee1a21e56
Source dataset
uspto-grants-1996_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05545835

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes