Pyridine → HCID 73455955, compound

HRID 1384780Notes

Reaction equation

HRID 1384780 reaction equation
[F:1][C:2]([F:25])([F:24])[C:3]([C:5]1[CH:10]=[CH:9][C:8]([O:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH3:23])=[CH:7][CH:6]=1)=O.[Cl-].[OH:27][NH3+:28].N1C=CC=CC=1>C(O)C>[F:1][C:2]([F:25])([F:24])[C:3]([C:5]1[CH:10]=[CH:9][C:8]([O:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH3:23])=[CH:7][CH:6]=1)=[N:28][OH:27]

Participants

5

Reactant 3

HCID 1049PyridineHCID 21645Hydroxylamine HClHCID 18674535HCID 18674535, compound

Product 1

HCID 73455955HCID 73455955, compoundYield 25.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

32 g (89.3 mmol) of 2,2,2-trifluoro-1-(4-dodecyloxyphenyl)-ethanone are dissolved in 200 ml of ethanol. To the solution are added 7.4 g (107 mmol) of hydroxylammonium chloride and 21.2 g (268 mmol) of pyridine. The reaction mixture is refluxed for 1.5 hours, and the solvent is distilled off by a rotary evaporator. The residue is poured into water, and extracted with ethyl acetate. The organic phase is washed with potassium hydrogen sulfate aqueous solution, water, and brine, dried over MgSO4, and concentrated. The residue is purified by recrystallization from hexane/toluene, yielding 8.4 g of 2,2,2-trifluoro-1-(4-dodecyloxyphenyl)-ethanone oxime as a white solid with a melting point of 70-72° C. The structure is confirmed by the 1H-NMR spectrum (CDCl3). δ[ppm]: 0.89 (t, 3H), 1.20-1.40 (m, 16H), 1.40-1.50 (m, 2H), 1.79 (m, 2H), 3.86-4.03 (m, 2H), 6.93(E)/6.97(Z) (d, 2H), 7.44(E)/7.53(Z) (d, 2H), 8.59(Z)/8.61 (E) (br s, 1H). The signals are tentatively assigned to the E- and Z-conformations. The spectrum indicates that the compound is a mixture of E- and Z-isomers. The ratio of the mixture is estimated to be E:Z=1:4.

Workup

  1. temperatureThe reaction mixture is refluxed for 1.5 hours
  2. distillationthe solvent is distilled off by a rotary evaporator
  3. additionThe residue is poured into water
  4. extractionextracted with ethyl acetate
  5. washThe organic phase is washed with potassium hydrogen sulfate aqueous solution, water, and brine
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated
  8. customThe residue is purified by recrystallization from hexane/toluene

Sources & evidence

ORD record
ord-87031a029e88461fbf0e162c13622f81
Source dataset
uspto-grants-2001_07
Patent number
US06261738B1

Reaction notes

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