Ethanol → HCID 178469094, compound

HRID 1690192Notes

Reaction equation

HRID 1690192 reaction equation
[OH:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][N:3]=1.C(=O)([O-])O.[Na+].[CH2:16](O)[CH3:17]>S(=O)(=O)(O)O>[OH:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([O:8][CH2:16][CH3:17])=[O:7])=[CH:4][N:3]=1

Participants

5

Reactant 3

HCID 702Ethanol2×HCID 516892Sodium BicarbonateHCID 178418479HCID 178418479, compound

Product 1

HCID 178469094HCID 178469094, compoundYield 89%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

To a solution of 6-hydroxynicotinic acid (5.0 g, 35.9 mmol) in ethanol (180 mL), sulfuric acid (1.0 mL) was added. The resultant mixture was stirred at 60° C. for 20 minutes, then added with surfuric acid (33.0 mL), and stirred for 6.5 hours while heated to reflux. The reaction solution was then added with a saturated aqueous solution of sodium hydrogen carbonate under ice-cold conditions and ethanol was concentrated in vacuo. After extracted with ethyl acetate, the organic layer was washed with brine, dried over sodium sulfate, and concentrated in vacuo. Ethyl 6-hydroxynicotinate (5.33 g, yield 89%) was obtained as a white crystal.

Workup

  1. temperaturewhile heated to reflux
  2. concentrationwas concentrated in vacuo
  3. extractionAfter extracted with ethyl acetate
  4. washthe organic layer was washed with brine
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-68c787a00e264f99b9cd3dc5256478cf
Source dataset
uspto-grants-2012_04
Patent number
US08153634B2

Reaction notes

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