Hydrochloric Acid → Ethyl 6-hydroxynicotinate

HRID 2080004Notes

Reaction equation

HRID 2080004 reaction equation
[OH:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][N:3]=1.Cl.C(=O)(O)[O-].[Na+].[CH2:17](O)[CH3:18]>>[CH2:17]([O:7][C:6]([C:5]1[CH:9]=[CH:10][C:2](=[O:1])[NH:3][CH:4]=1)=[O:8])[CH3:18]

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 702EthanolHCID 516892Sodium BicarbonateHCID 178418479HCID 178418479, compound

Product 1

HCID 295861Ethyl 6-hydroxynicotinateYield 65%

Conditions

Temperature
110 °C

Procedure

To a suspension of 6-hydroxy-nicotinic acid (5.00 g, 35.9 mmol) in ethanol (60 mL) was added 1N hydrochloric acid (20 mL), which was then stirred at 110° C. for 3 hours. The reaction solution was cooled to 0° C., then, an aqueous solution of saturated sodium bicarbonate was added, the solution was extracted with ethyl acetate and tetrahydrofuran, and the organic layer was dried over anhydrous magnesium sulfate. The solvent was evaporated in vacuo, the residue was purified by silica gel column chromatography (ethyl acetate), and the title compound (3.90 g, 23.3 mmol, 65%) was obtained as a white solid.

Workup

  1. temperatureThe reaction solution was cooled to 0° C.
  2. extractionthe solution was extracted with ethyl acetate and tetrahydrofuran
  3. dry with materialthe organic layer was dried over anhydrous magnesium sulfate
  4. customThe solvent was evaporated in vacuo
  5. customthe residue was purified by silica gel column chromatography (ethyl acetate)

Sources & evidence

ORD record
ord-f3786a8e0e5d4e75956a0988b796ee80
Source dataset
uspto-grants-2011_04
Patent number
US07932272B2

Reaction notes

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