4-Fluoroaniline → HCID 57951168, compound

HRID 1919793Notes

Reaction equation

HRID 1919793 reaction equation
[F:1][C:2]([F:13])([F:12])[O:3][C:4]1[CH:5]=[C:6]([CH:9]=[CH:10][CH:11]=1)[CH:7]=O.[F:14][C:15]1[CH:21]=[CH:20][C:18]([NH2:19])=[CH:17][CH:16]=1.[C:22]([O:27]CC)(=O)[C:23]([CH3:25])=O>C(O)(=O)C>[F:1][C:2]([F:13])([F:12])[O:3][C:4]1[CH:5]=[C:6]([CH:7]2[N:19]([C:18]3[CH:20]=[CH:21][C:15]([F:14])=[CH:16][CH:17]=3)[C:22](=[O:27])[C:23]([NH:19][C:18]3[CH:20]=[CH:21][C:15]([F:14])=[CH:16][CH:17]=3)=[CH:25]2)[CH:9]=[CH:10][CH:11]=1

Participants

5

Reactant 3

HCID 97314-FluoroanilineHCID 12041Ethyl pyruvateHCID 6051393-(Trifluoromethoxy)benzaldehyde

Product 1

HCID 57951168HCID 57951168, compoundYield 60%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

Stir 3-(trifluoromethoxy)benzaldehyde (15.0 g, 78.6 mmol), 4-fluoroaniline (22.4 mL, 236 mmol) and ethyl pyruvate (8.65 mL, 78.6 mmol) in glacial acetic acid (60 mL) at ambient temperature for 72 hours. Filter the precipitate and wash with a 3:1 heptane/MTBE mixture. Dry under vacuum to afford the titled compound (20.9 g, 60%) as an off-white powder: MS (m/z): 445 (M−1).

Workup

  1. filtrationFilter the precipitate
  2. washwash with a 3:1 heptane/MTBE mixture
  3. customDry under vacuum

Sources & evidence

ORD record
ord-9d226e2e1cc04f6cb5f5e07d24772d8e
Source dataset
uspto-grants-2012_05
Patent number
US08168659B2

Reaction notes

Loading…