Quinoline → 2,4,5-Trifluorobenzoic acid

HRID 1493536Notes

Reaction equation

HRID 1493536 reaction equation
[F:1][C:2]1[C:10](C(O)=O)=[C:9]([F:14])[C:8]([F:15])=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].N1C2C(=CC=CC=2)C=CC=1>[Cu]>[F:1][C:2]1[CH:10]=[C:9]([F:14])[C:8]([F:15])=[CH:7][C:3]=1[C:4]([OH:6])=[O:5]

Participants

4

Reactant 2

HCID 7047QuinolineHCID 14596967HCID 14596967, compound

Product 1

HCID 5211702,4,5-Trifluorobenzoic acid

Reagents, catalysts & solvents 1

HCID 23978CopperCatalyst

Procedure

A mixture of 2.20 g (0.01 mole) of 2,4,5-trifluoroisophthalic acid (dried under high vacuum). 1.0 ml of quinoline and 0.23 g of copper powder was heated on an oil bath at 200° C. After a while, the mixture liquefied and released a gas (ca. 280 ml by top purging). After the gas had been completely released, the liquefied mixture was cooled to room temperature, followed by addition of 15 ml of a mixture (1:1 by weight) of conc. HCl and water.

Workup

  1. customa gas (ca. 280 ml by top purging)
  2. additionfollowed by addition of 15 ml of a mixture (1:1 by weight) of conc. HCl and water

Sources & evidence

ORD record
ord-5a69584ba707416e9b0a9f456a83953d
Source dataset
uspto-grants-1991_06
Patent number
US05021605

Reaction notes

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