Thionyl Chloride → Methyl 5-hydroxypyridine-3-carboxylate

HRID 1496978Notes

Reaction equation

HRID 1496978 reaction equation
[OH:1][C:2]1[CH:3]=[N:4][CH:5]=[C:6]([CH:10]=1)[C:7]([OH:9])=[O:8].S(Cl)(Cl)=O.[C:15]([O-])(O)=O.[Na+]>CO>[OH:1][C:2]1[CH:3]=[N:4][CH:5]=[C:6]([CH:10]=1)[C:7]([O:9][CH3:15])=[O:8]

Participants

5

Reactant 3

HCID 24386Thionyl ChlorideHCID 340375-Hydroxynicotinic acidHCID 516892Sodium Bicarbonate

Product 1

HCID 354317Methyl 5-hydroxypyridine-3-carboxylate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a stirred solution of 5-hydroxynicotinic acid (10 g, 71.9 mmol) in MeOH (100 mL) was added sulfurous dichloride (1 mL) drop wise over 5 min. The resulting mixture was stirred at room temperature overnight. The resulted solution was added 100 mL of NaHCO3. The precipitate was filtrated and washed with MeOH for several cycles to give 8.5 g of A031-2 (75% yields), which was used for the nest step without further purification.

Workup

  1. filtrationThe precipitate was filtrated
  2. washwashed with MeOH for several cycles
  3. customto give
  4. custom8.5 g of A031-2 (75% yields), which
  5. customwas used for the nest step without further purification

Sources & evidence

ORD record
ord-f0d60d23922c453f97329eff6f7c8133
Source dataset
uspto-grants-2015_12
Patent number
US09199947B2

Reaction notes

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