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

HRID 2175558Notes

Reaction equation

HRID 2175558 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-7dd8d3f1c15b45d78afc209e430f5e2f
Source dataset
uspto-grants-2015_06
Patent number
US09062048B2

Reaction notes

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