Thionyl Chloride → Methyl 5-hydroxypyridine-3-carboxylate

HRID 1746452Notes

Reaction equation

HRID 1746452 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-efb53ed094bb4b09a9a112f797b9ab5d
Source dataset
uspto-grants-2015_10
Patent number
US09150526B2

Reaction notes

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