3-(Trifluoromethyl)aniline → HCID 21110147, compound

HRID 1766362Notes

Reaction equation

HRID 1766362 reaction equation
[CH:1]([C:3]1[CH:10]=[CH:9][C:6]([C:7]#[N:8])=[CH:5][CH:4]=1)=O.[O:11]=[C:12]([CH3:20])[CH2:13][C:14]([O:16][CH2:17][CH:18]=[CH2:19])=[O:15].C[C:22]1([CH3:30])[O:27]C(=O)CC(=O)O1.[F:31][C:32]([F:41])([F:40])[C:33]1[CH:34]=[C:35]([CH:37]=[CH:38][CH:39]=1)[NH2:36].[F-].[K+]>C1COCC1>[C:12]([CH:13]([CH:1]([C:3]1[CH:10]=[CH:9][C:6]([C:7]#[N:8])=[CH:5][CH:4]=1)[CH2:30][C:22](=[O:27])[NH:36][C:35]1[CH:37]=[CH:38][CH:39]=[C:33]([C:32]([F:31])([F:40])[F:41])[CH:34]=1)[C:14]([O:16][CH2:17][CH:18]=[CH2:19])=[O:15])(=[O:11])[CH3:20]

Participants

7

Reactant 5

HCID 73753-(Trifluoromethyl)anilineHCID 162492,2-Dimethyl-1,3-dioxane-4,6-dioneHCID 660424-CyanobenzaldehydeHCID 70701Allyl acetoacetateHCID 522689Potassium Fluoride

Product 1

HCID 21110147HCID 21110147, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4-formylbenzonitrile (10.00 g, 76.3 mmol), allyl 3-oxobutanoate (10.84 g, 76.3 mmol), 2,2-dimethyl-1,3-dioxane-4,6-dione (10.99 g, 76.3 mmol) and 3-(trifluoromethyl)aniline (12.29 g, 76.3 mmol) in 150 ml THF are added 4.00 g potassium fluoride on alumina (40 wt.-%). The reaction mixture is stirred at reflux temperature overnight. The solvent is removed in vacuo, the residue is dissolved in methylene chloride and then purified by column chromatography using a methylene chloride/ethyl acetate gradient as eluent.

Workup

  1. temperatureat reflux temperature overnight
  2. customThe solvent is removed in vacuo
  3. dissolutionthe residue is dissolved in methylene chloride
  4. custompurified by column chromatography

Sources & evidence

ORD record
ord-e4346b62e26240468aa6c8f972f14679
Source dataset
uspto-grants-2007_06
Patent number
US07230017B2

Reaction notes

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