Acetyl chloride → Phenyl[4-Phenyl-8-(Trifluoromethyl)Quinolin-3-yl]Methyl Acetate

HRID 2104494Notes

Reaction equation

HRID 2104494 reaction equation
[C:1]1([CH:7]([C:9]2[CH:10]=[N:11][C:12]3[C:17]([C:18]=2[C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[CH:16][CH:15]=[CH:14][C:13]=3[C:25]([F:28])([F:27])[F:26])[OH:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(N(CC)CC)C.[C:36](Cl)(=[O:38])[CH3:37]>C(Cl)Cl>[C:36]([O:8][CH:7]([C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)[C:9]1[CH:10]=[N:11][C:12]2[C:17]([C:18]=1[C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1)=[CH:16][CH:15]=[CH:14][C:13]=2[C:25]([F:28])([F:26])[F:27])(=[O:38])[CH3:37]

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 11222693Phenyl[4-Phenyl-8-(Trifluoromethyl)Quinolin-3-yl]Methanol

Product 1

HCID 66914489Phenyl[4-Phenyl-8-(Trifluoromethyl)Quinolin-3-yl]Methyl AcetateYield 79.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Phenyl[4-phenyl-8-(trifluoromethyl)quinolin-3-yl]methanol (Example 34, 0.050 g, 0.132 mmol) was taken into CH2Cl2 (3 mL). Next, triethylamine (0.1 mL, 0.70 mmol) was added followed by acetyl chloride (0.05 mL, 0.70 mmol). The reaction was allowed to stir for 2 hours. The solvent was removed and the resulting material was taken up into an Ether/water/5% HCl solution. The layers were separated and the organic layer was washed once more with 5% HCl, dried over magnesium sulfate and concentrated. The product was purified via column chromatography using 7% ethyl acetate in hexane as the eluent to afford the product as a white solid (0.044 g, 79.4%). MS (ESI) m/z 422 ([M+H]+); Anal. Calcd. for C25H18F3NO2: C, 71.25; H, 4.31; N, 3.32. Found: C, 71.15; H, 4.11; N, 3.21.

Workup

  1. customThe solvent was removed
  2. customThe layers were separated
  3. washthe organic layer was washed once more with 5% HCl
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated
  6. customThe product was purified via column chromatography

Sources & evidence

ORD record
ord-f88f7d3578f24dc594df7b4f93372a09
Source dataset
uspto-grants-2009_08
Patent number
US07576215B2

Reaction notes

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