Hydrochloric Acid → Ethyl 2-[(3-hydroxypyridin-2-yl)oxy]acetate

HRID 1862334Notes

Reaction equation

HRID 1862334 reaction equation
C([O:4][C:5]1[C:6]([O:11][CH2:12][C:13]([O:15][CH2:16][CH3:17])=[O:14])=[N:7][CH:8]=[CH:9][CH:10]=1)(=O)C.C(=O)([O-])[O-].[K+].[K+].[Cl-].[Na+].Cl>O.C(O)C>[OH:4][C:5]1[C:6]([O:11][CH2:12][C:13]([O:15][CH2:16][CH3:17])=[O:14])=[N:7][CH:8]=[CH:9][CH:10]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 5234Sodium ChlorideHCID 11430Potassium CarbonateHCID 186191663-Acetoxy-2-(ethoxycarbonyl)methoxypyridine

Product 1

HCID 18619272Ethyl 2-[(3-hydroxypyridin-2-yl)oxy]acetateYield 91.9%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

A mixture of 13.8 g of 3-acetoxy-2-(ethoxycarbonyl)methoxypyridine, 4.38 g of potassium carbonate and 60 ml of ethanol was stirred for over night at room temperature. The reaction solution was poured into a mixture of water, sodium chloride and hydrochloric acid, and extracted with ethyl acetate. The organic layer was washed with saturated saline, dried over anhydrous magnesium sulfate, and concentrated. The residue was subjected to silica gel column chromatography to obtain 10.45 g of 3-hydroxy-2-(ethoxycarbonyl)methoxypyridine.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with saturated saline
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-01752d22f9a74394bb7666eb658513db
Source dataset
uspto-grants-2003_03
Patent number
US06537948B1

Reaction notes

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