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

HRID 1788917Notes

Reaction equation

HRID 1788917 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. (]42 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 1.6 M 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-8ec6bc0ba583456dba19b4ce1259fcc1
Source dataset
uspto-grants-1987_08
Patent number
US04686222

Reaction notes

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