Ethanol → HCID 178469094, compound

HRID 657597Notes

Reaction equation

HRID 657597 reaction equation
[OH:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][N:3]=1.S(=O)(=O)(O)O.[CH2:16](O)[CH3:17]>>[CH2:16]([O:7][C:6](=[O:8])[C:5]1[CH:9]=[CH:10][C:2]([OH:1])=[N:3][CH:4]=1)[CH3:17]

Participants

4

Reactant 3

HCID 702EthanolHCID 1118Sulfuric AcidHCID 178418479HCID 178418479, compound

Product 1

HCID 178469094HCID 178469094, compoundYield 80%

Procedure

To a 100 mL three-necked flask, 0.84 g (0.006 mol) of 6-hydroxynicotinic acid, 30 mL of anhydrous ethanol were added, 3 mL of concentrated sulfuric acid was added dropwise slowly, refluxed overnight, evaporated under vacuum to remove excessive ethanol, the residue was poured into water, extracted with ethyl acetate, washed with saturated sodium hydrogen carbonate, dried with anhydrous sodium sulfate, and concentrated to obtain 0.8 g of 6-hydroxy-nicotinic acid ethyl ester. Yield: 80%.

Workup

  1. temperaturerefluxed overnight
  2. customevaporated under vacuum
  3. customto remove excessive ethanol
  4. additionthe residue was poured into water
  5. extractionextracted with ethyl acetate
  6. washwashed with saturated sodium hydrogen carbonate
  7. dry with materialdried with anhydrous sodium sulfate
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-cceb857afbcd4c9baf619af6d8f86756
Source dataset
uspto-grants-2011_12
Patent number
US08076339B2

Reaction notes

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