Trifluoroacetic acid → 2-Quinolinecarbonitrile, 4-hydroxy-6-(trifluoromethyl)-

HRID 1896877Notes

Reaction equation

HRID 1896877 reaction equation
COC1C=CC(C[O:8][C:9]2[C:18]3[C:13](=[CH:14][CH:15]=[C:16]([C:19]([F:22])([F:21])[F:20])[CH:17]=3)[N:12]=[C:11]([C:23]#[N:24])[CH:10]=2)=CC=1.C(O)(C(F)(F)F)=O>C(Cl)Cl>[OH:8][C:9]1[C:18]2[C:13](=[CH:14][CH:15]=[C:16]([C:19]([F:22])([F:20])[F:21])[CH:17]=2)[N:12]=[C:11]([C:23]#[N:24])[CH:10]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 585625264-((4-Methoxybenzyl)oxy)-6-(trifluoromethyl)quinoline-2-carbonitrile

Product 1

HCID 1785102352-Quinolinecarbonitrile, 4-hydroxy-6-(trifluoromethyl)-

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 4-((4-methoxybenzyl)oxy)-6-(trifluoromethyl)quinoline-2-carbonitrile (5 g, 14 mmol) from above step C, in 15 mL DCM and 45 mL TFA was stirred for 2 h. Solvent was removed under vacuum and the residue was evaporated form toluene twice. The residue was dried under high vacuum. The resulting yellow solid was triturated with hot toluene, filtered and washed with ether to provide the title compound as a white solid.

Workup

  1. customSolvent was removed under vacuum
  2. customthe residue was evaporated form toluene twice
  3. customThe residue was dried under high vacuum
  4. customThe resulting yellow solid was triturated with hot toluene
  5. filtrationfiltered
  6. washwashed with ether

Sources & evidence

ORD record
ord-fbda21aea63f4c07bf125f1f216dfe7a
Source dataset
uspto-grants-2013_08
Patent number
US08518969B2

Reaction notes

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