Ammonium Hydroxide → 3-{[3-Benzyl-8-(Trifluoromethyl)Quinolin-4-yl]Methyl}Phenol

HRID 2104798Notes

Reaction equation

HRID 2104798 reaction equation
[CH2:1]([C:8]1[CH:9]=[N:10][C:11]2[C:16]([C:17]=1[CH:18]([C:21]1[CH:26]=[CH:25][CH:24]=[C:23]([O:27]C)[CH:22]=1)C#N)=[CH:15][CH:14]=[CH:13][C:12]=2[C:29]([F:32])([F:31])[F:30])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[NH4+]>Br.O>[CH2:1]([C:8]1[CH:9]=[N:10][C:11]2[C:16]([C:17]=1[CH2:18][C:21]1[CH:22]=[C:23]([OH:27])[CH:24]=[CH:25][CH:26]=1)=[CH:15][CH:14]=[CH:13][C:12]=2[C:29]([F:31])([F:32])[F:30])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 14923Ammonium HydroxideHCID 66913948[3-Benzyl-8-(trifluoromethyl)quinolin-4-yl](3-methoxyphenyl)acetonitrile

Product 1

HCID 669138793-{[3-Benzyl-8-(Trifluoromethyl)Quinolin-4-yl]Methyl}PhenolYield 84%

Reagents, catalysts & solvents 2

HCID 260Hydrogen BromideSolventHCID 962WaterSolvent

Procedure

[3-Benzyl-8-(trifluoromethyl)quinolin-4-yl](3-methoxyphenyl)acetonitrile (5.14 g, 11.88 mmol) in 48% HBr (75 mL) is heated at 90° C. for 65 h. Cooled reaction is poured into concentrated ammonium hydroxide (50 mL) diluted with water and ice. The mixture is extracted with ethyl acetate and the combined extracts are dried (MgSO4) and concentrated. The residue is purified via column chromatography using 15:85 ethyl acetate:hexane as the eluent to afford the title compound as a yellow powder (3.91 g, 84%). HRMS: calcd for C24H18F3NO+H+, 394.14132; found (ESI, [M+H]+), 394.1404.

Workup

  1. temperatureCooled
  2. customreaction
  3. extractionThe mixture is extracted with ethyl acetate
  4. dry with materialthe combined extracts are dried (MgSO4)
  5. concentrationconcentrated
  6. customThe residue is purified via column chromatography

Sources & evidence

ORD record
ord-229cdb3c9f1240edaec7a881e01f5266
Source dataset
uspto-grants-2009_08
Patent number
US07576215B2

Reaction notes

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