4-(Trifluoromethyl)aniline → N-[4-(trifluoromethyl)phenyl]-3-oxopentanoic acid amide

HRID 1354536Notes

Reaction equation

HRID 1354536 reaction equation
[O:1]=[C:2]([CH2:8][CH3:9])[CH2:3][C:4]([O:6]C)=O.[F:10][C:11]([F:20])([F:19])[C:12]1[CH:18]=[CH:17][C:15]([NH2:16])=[CH:14][CH:13]=1>C1(C)C=CC=CC=1>[F:10][C:11]([F:19])([F:20])[C:12]1[CH:13]=[CH:14][C:15]([NH:16][C:4](=[O:6])[CH2:3][C:2](=[O:1])[CH2:8][CH3:9])=[CH:17][CH:18]=1

Participants

4

Reactant 2

HCID 99644-(Trifluoromethyl)anilineHCID 121699Methyl 3-oxovalerate

Product 1

HCID 11961981N-[4-(trifluoromethyl)phenyl]-3-oxopentanoic acid amideYield 57%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
0 °C

Procedure

Methyl 3-oxopentanoate 10.0 g (76.8 mmol) was heated to 115° C. and 4-(trifluoromethyl)aniline 12.83 g (79.6 mmol) was added dropwise thereto for 10 minutes. After stirring at the same temperature for 25 minutes, toluene (50 mL) was added and the resulting reaction solution was further heated and stirred for 12 hours. The reaction solution was cooled to 0° C. to precipitate a solid and subjected to vacuum filtration to obtain N-[4-(trifluoromethyl)phenyl]-3-oxopentanoic acid amide as a white solid (11.22 g, isolated yield: 57%). 1H-NMR (CDCl3, 400 MHz/ppm): δ 1.13 (3H, t), 2.64 (2H, q), 3.60 (2H, s), 7.58 (2H, d), 7.69 (2H, d), 9.52 (1H, br)

Workup

  1. customthe resulting reaction solution
  2. temperaturewas further heated
  3. stirringstirred for 12 hours
  4. customto precipitate a solid
  5. filtrationsubjected to vacuum filtration
  6. customto obtain

Sources & evidence

ORD record
ord-86a3e9ce5d7e492eac4b3c45458b497b
Source dataset
uspto-grants-2007_05
Patent number
US07223859B2

Reaction notes

Loading…