Hydrochloric Acid → Ethyl 5-fluoropyridine-2-carboxylate

HRID 1791354Notes

Reaction equation

HRID 1791354 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]([OH:10])=[O:9])=[N:6][CH:7]=1.[CH2:11](O)[CH3:12].Cl>O1CCOCC1>[CH2:11]([O:9][C:8]([C:5]1[CH:4]=[CH:3][C:2]([F:1])=[CH:7][N:6]=1)=[O:10])[CH3:12]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 702EthanolHCID 27628765-fluoropyridine-2-carboxylic Acid

Product 1

HCID 10986675Ethyl 5-fluoropyridine-2-carboxylateYield 49.3%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

5-Fluoro-pyridine-2-carboxylic acid (200 mg, 1.13 mmol) was mixed with ethanol (6 mL) and 4 M HCl in dioxane (0.5 mL) at 90° C. for 20 h. The mixture was concentrated and mixed with saturated sodium carbonate and dichloromethane. The dichloromethane layer was washed with brine, dried to give 94 mg (49.3%) of 5-fluoro-pyridine-2-carboxylic acid ethyl ester.

Workup

  1. concentrationThe mixture was concentrated
  2. additionmixed with saturated sodium carbonate and dichloromethane
  3. washThe dichloromethane layer was washed with brine
  4. customdried

Sources & evidence

ORD record
ord-e1f40f47ba5b4ffdb0a8c6d6403695d0
Source dataset
uspto-grants-2006_07
Patent number
US07074809B2

Reaction notes

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