Potassium Iodide → HCID 22416892, compound

HRID 1721171Notes

Reaction equation

HRID 1721171 reaction equation
[F:1][C:2]([F:23])([F:22])[C:3]1[CH:12]=[C:11]2[C:6]([CH:7]=[CH:8][C:9]([CH2:13][O:14][C:15]3[CH:16]=[C:17]([CH:19]=[CH:20][CH:21]=3)[NH2:18])=[N:10]2)=[CH:5][CH:4]=1.[C:24](=[O:27])([O-])[O-:25].[Na+].[Na+].N[C:31]1C=[C:33]([OH:37])[CH:34]=[CH:35][CH:36]=1.Br[CH2:39][C:40]1C=CC2C(=CC(C(F)(F)F)=CC=2)N=1.C(=O)([O-])[O-].[Cs+].[Cs+].[I-].[K+]>CC(C)=O>[F:23][C:2]([F:22])([F:1])[C:3]1[CH:12]=[C:11]2[C:6]([CH:7]=[CH:8][C:9]([CH2:13][O:14][C:15]3[CH:16]=[C:17]([NH:18][C:33](=[O:37])[CH2:34][C:35]([CH2:36][CH3:31])([CH2:39][CH3:40])[C:24]([OH:25])=[O:27])[CH:19]=[CH:20][CH:21]=3)=[N:10]2)=[CH:5][CH:4]=1

Participants

8

Reactant 6

HCID 4875Potassium IodideHCID 10340Sodium CarbonateHCID 10796Cesium carbonateHCID 115683-AminophenolHCID 22416884HCID 22416884, compoundHCID 22416911HCID 22416911, compound

Product 1

HCID 22416892HCID 22416892, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

3-(7-trifluoromethyl-2-quinolinylmethoxy)aniline: 3.0 g of sodium carbonate are added to a solution of 2.0 g of 3-aminophenol in 200 ml of acetone and the mixture is stirred for 15 min. at 50°. 5.2 g of 2-bromomethyl-7-trifluoromethylquinoline, 6.1 g of caesium carbonate and 0.1 g of potassium iodide are added thereto and boiling under reflux is carried out for 2 hours. The reaction mixture is filtered, the precipitate is washed with acetone and the filtrate is concentrated by evaporation. The residue is taken up in hexane/ethyl acetate 3:2 and filtered over silica gel. The filtrate is concentrated by evaporation and the resulting oil is chromatographed on 400 g of silica gel using hexane/ethyl acetate 3:2. The title compound is obtained in the form of a yellow solid of m.p. 85°-86°.

Workup

  1. temperatureunder reflux
  2. waitis carried out for 2 hours
  3. filtrationThe reaction mixture is filtered
  4. washthe precipitate is washed with acetone
  5. concentrationthe filtrate is concentrated by evaporation
  6. filtrationfiltered over silica gel
  7. concentrationThe filtrate is concentrated by evaporation
  8. customthe resulting oil is chromatographed on 400 g of silica gel

Sources & evidence

ORD record
ord-6e33bda317404099a1ec3d2f5b60a07a
Source dataset
uspto-grants-1996_04
Patent number
US05508408

Reaction notes

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