Sodium Sulfite → 5-Hydroxy-6-methylpyridine-2-carboxylic acid

HRID 2204230Notes

Reaction equation

HRID 2204230 reaction equation
C[O:2][C:3]1[CH:4]=[CH:5][C:6]([C:10]([OH:12])=[O:11])=[N:7][C:8]=1[CH3:9].I.[O-]S([O-])=O.[Na+].[Na+]>O>[OH:2][C:3]1[CH:4]=[CH:5][C:6]([C:10]([OH:12])=[O:11])=[N:7][C:8]=1[CH3:9]

Participants

5

Reactant 3

HCID 24437Sodium SulfiteHCID 24841Hydrogen iodideHCID 281704HCID 281704, compound

Product 1

HCID 2817035-Hydroxy-6-methylpyridine-2-carboxylic acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 5-methoxy-6-methyl-pyridine-2-carboxylic acid (53 mg, 0.32 mmol) and hydrogen iodide (2.06 mL of 57% w/v, 9.20 mmol) was heated at reflux for 4 hours. The reaction was cooled to room temperature before water (3 mL) was added. Na2SO3 was added to decolorize the reaction. The aqueous layer was decanted and the pH was adjusted to 3-4 using 2 M HCl. The product was extracted using ethyl acetate (7×5 mL). The organic layer was dried over sodium sulfate, filtered and the solvent was evaporated under reduced pressure to yield 5-hydroxy-6-methylpicolinic acid. ESI-MS m/z calc. 153.0, found 154.1 (M+1)+; Retention time: 0.21 minutes (3 min run).

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 4 hours
  3. additionwas added
  4. customthe reaction
  5. customThe aqueous layer was decanted
  6. extractionThe product was extracted
  7. dry with materialThe organic layer was dried over sodium sulfate
  8. filtrationfiltered
  9. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-fe287f76df6d4ab495a09c2bbe483d41
Source dataset
uspto-grants-2016_06
Patent number
US09365588B2

Reaction notes

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