6-Fluoronicotinic Acid → 1-(6-Fluoropyridin-3-yl)ethan-1-one

HRID 1589144Notes

Reaction equation

HRID 1589144 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([OH:10])=O)=[CH:4][N:3]=1.[CH3:11][Li]>CCOCC>[C:8]([C:5]1[CH:6]=[CH:7][C:2]([F:1])=[N:3][CH:4]=1)(=[O:10])[CH3:11]

Participants

4

Reactant 2

HCID 2428196-Fluoronicotinic AcidHCID 178418348HCID 178418348, compound

Product 1

HCID 130903391-(6-Fluoropyridin-3-yl)ethan-1-one

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

To suspension of 20 gm. (142 mmoles) of 2-fluoro-5-pyridinecarboxylic acid (J. Am. Chem. Soc., 71, 1125 (1949)) in 750 ml. of ether, stirred and cooled in ice, was added 225 ml. of 1.6M methyl lithium (360 mmoles) in ether over 1 hr. The reaction was stirred for an additional 2 hr., then 300 ml. of ice water was added. The aqueous layer was washed with 2×100 ml. fresh ether, acidified and extracted with ether to give 5.0 gm. (25%) of unreacted starting acid.

Workup

  1. additionTo suspension of 20 gm
  2. temperaturecooled in ice
  3. additionwas added 225 ml
  4. washThe aqueous layer was washed with 2×100 ml
  5. extractionextracted with ether
  6. customto give 5.0 gm

Sources & evidence

ORD record
ord-38b13558b83045acaf9e380a024e213e
Source dataset
uspto-grants-1986_02
Patent number
US04568679

Reaction notes

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