Methanol → Pyridine-3,5-dicarboxylic acid methyl ester hydrochloride

HRID 365437

Reaction equation

HRID 365437 reaction equation
[N:1]1[CH:6]=[C:5]([C:7]([OH:9])=[O:8])[CH:4]=[C:3]([C:10]([OH:12])=[O:11])[CH:2]=1.S(Cl)([Cl:15])=O.[CH3:17]O>>[ClH:15].[CH3:17][O:8][C:7]([C:5]1[CH:6]=[N:1][CH:2]=[C:3]([C:10]([OH:12])=[O:11])[CH:4]=1)=[O:9]

Participants

4

Reactant 3

HCID 887MethanolHCID 103663,5-Pyridinedicarboxylic acidHCID 24386Thionyl Chloride

Product 1

HCID 70274642Pyridine-3,5-dicarboxylic acid methyl ester hydrochloride

Procedure

Pyridine-3,5-dicarboxylic acid (5.00 g, 29.9 mmol) was stirred in CH3OH (100 mL), cooled in an ice bath, and treated dropwise with thionyl chloride (17.45 mL, 239.2 mmol). After 0.5 hr, the reaction mixture was refluxed for 48 hrs. Concentration to dryness gave the title compound as an off-white solid.

Workup

  1. temperaturecooled in an ice bath
  2. temperaturethe reaction mixture was refluxed for 48 hrs
  3. concentrationConcentration to dryness

Sources & evidence

ORD record
ord-1b62a4aa5e3545ef8cc070eb914f7418
Source dataset
uspto-grants-2000_10
Patent number
US06127366

Linked notes

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