Methane → HCID 68550158, compound

HRID 731709Notes

Reaction equation

HRID 731709 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[N:20]O)[CH2:9][C:10]2[CH:15]=[CH:14][C:13]([C:16]([F:19])([F:18])[F:17])=[CH:12][N:11]=2)=[CH:4][CH:3]=1.FC1C=[CH:27][C:26]([C:29](=[O:41])CC2C=CC(C(F)(F)F)=CN=2)=[CH:25]C=1.[OH-].[Na+].Cl.NO.C>CO>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:9]([C:29](=[O:41])[CH:26]([CH3:27])[CH3:25])=[C:10]3[CH:15]=[CH:14][C:13]([C:16]([F:19])([F:18])[F:17])=[CH:12][N:11]3[N:20]=2)=[CH:4][CH:3]=1

Participants

7

Reactant 5

HCID 297MethaneHCID 14798Sodium HydroxideHCID 443297Hydroxyamine hydrochlorideHCID 18987643Ethanone, 1-(4-fluorophenyl)-2-[5-(trifluoromethyl)-2-pyridinyl]-HCID 73025893HCID 73025893, compound

Product 1

HCID 68550158HCID 68550158, compoundYield 59%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
0 °C

Procedure

1-(4-fluorophenyl)-2-(5-(trifluoromethyl)pyridin-2-yl)ethanone oxime. To a solution of 1-(4-fluorophenyl)-2-(5-(trifluoromethyl)pyridin-2-yl)ethanone (8.00 g, 28.2 mmol) in methanol (100 ml) at room temperature was added 15% NaOH (29 ml, 109 mmol). The resulting solution was stirred vigorously as solid hydroxylamine hydrochloride (9.8 g, 140 mmol) was added portionwise. The mixture was heated to reflux for 1 hour, treated with charcoal while hot, and then quickly filtered through Celite before being allowed to cool. The filtrate was concentrated to one-half of its original volume and then cooled to 0° C. for 1 hour. The resultant solids were collected by filtration, washed with water, and dried under vacuum at 50° C. overnight to provide 5.00 g (59%) of the title compound as a dark yellow solid.

Workup

  1. additionwas added portionwise
  2. temperatureThe mixture was heated
  3. temperatureto reflux for 1 hour
  4. filtrationthen quickly filtered through Celite
  5. temperatureto cool
  6. concentrationThe filtrate was concentrated to one-half of its original volume
  7. filtrationThe resultant solids were collected by filtration
  8. washwashed with water
  9. customdried under vacuum at 50° C. overnight

Sources & evidence

ORD record
ord-8b1bb8cd1b9048ad85af22b9306f8e86
Source dataset
uspto-grants-2009_09
Patent number
US07585875B2

Reaction notes

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