Trifluoroacetic acid → HCID 58875319, compound

HRID 2079986Notes

Reaction equation

HRID 2079986 reaction equation
C1(SC)C=CC=CC=1.C([O:16][C:17]1[CH:18]=[C:19]([CH:34]=[CH:35][CH:36]=1)[CH2:20][NH:21][C:22]([C:24]1[CH:25]=[C:26]2[C:31](=[CH:32][CH:33]=1)[N:30]=[CH:29][CH:28]=[CH:27]2)=[O:23])C1C=CC=CC=1.FC(F)(F)C(O)=O>>[OH:16][C:17]1[CH:18]=[C:19]([CH:34]=[CH:35][CH:36]=1)[CH2:20][NH:21][C:22]([C:24]1[CH:25]=[C:26]2[C:31](=[CH:32][CH:33]=1)[N:30]=[CH:29][CH:28]=[CH:27]2)=[O:23]

Participants

4

Reactant 3

HCID 6422Trifluoroacetic acidHCID 7520ThioanisoleHCID 58387971HCID 58387971, compound

Product 1

HCID 58875319HCID 58875319, compoundYield 64%

Procedure

Thioanisole (1.7 mL, 14 mmol) was added to a mixture of quinoline-6-carboxylic acid 3-benzyloxybenzylamide (1.3 g, 3.6 mmol) and trifluoroacetic acid(8 mL) on an ice bath, and the solution was stirred for 4 hours at room temperature. The solvent was evaporated in vacuo, then water, an aqueous solution of saturated sodium bicarbonate, ethyl acetate and tetrahydrofuran were added to the residue for extraction, the organic layer was washed with brine, then, dried over anhydrous magnesium sulfate. The solvent was evaporated in vacuo, recrystallized from ethyl acetate-methanol, and the title compound (0.64 g, 2.3 mmol, 64%) was obtained as a white crystal.

Workup

  1. customThe solvent was evaporated in vacuo
  2. additionwater, an aqueous solution of saturated sodium bicarbonate, ethyl acetate and tetrahydrofuran were added to the residue for extraction
  3. washthe organic layer was washed with brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customThe solvent was evaporated in vacuo
  6. customrecrystallized from ethyl acetate-methanol

Sources & evidence

ORD record
ord-e54cd82d082c4582ab4288ce20241e34
Source dataset
uspto-grants-2011_04
Patent number
US07932272B2

Reaction notes

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