4-(Trifluoromethyl)phenylacetonitrile → HCID 57600293, compound

HRID 1664557Notes

Reaction equation

HRID 1664557 reaction equation
[F:1][C:2]([F:13])([F:12])[C:3]1[CH:8]=[CH:7][C:6]([CH2:9][C:10]#[N:11])=[CH:5][CH:4]=1.Cl.[NH2:15][OH:16].C([O-])(O)=O.[Na+]>CO>[OH:16]/[N:15]=[C:10](\[NH2:11])/[CH2:9][C:6]1[CH:5]=[CH:4][C:3]([C:2]([F:12])([F:1])[F:13])=[CH:8][CH:7]=1

Participants

5

Reactant 3

HCID 753594-(Trifluoromethyl)phenylacetonitrileHCID 443297Hydroxyamine hydrochlorideHCID 516892Sodium Bicarbonate

Product 1

HCID 57600293HCID 57600293, compoundYield 84.9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A suspension of [4-(trifluoromethyl)phenyl]acetonitrile (1.0 g, 5.4 mmoles), hydroxylamine hydrochloride (0.41 g, 5.9 mmoles) and NaHCO3 (0.50 g, 5.9 mmoles) in MeOH (15 ml) was refluxed for 4 hours. The reaction mixture was then concentrated to remove the solvent methanol. The residue was extracted with ethyl acetate. The combined organic layers were washed with brine and dried over Na2SO4 and concentrated to afford the desired product (1.0 g, 84.9%) as white solid. LCMS calculated for C9H10F3N2O (M+H): 219.1. found: 219.1.

Workup

  1. temperaturewas refluxed for 4 hours
  2. concentrationThe reaction mixture was then concentrated
  3. customto remove the solvent methanol
  4. extractionThe residue was extracted with ethyl acetate
  5. washThe combined organic layers were washed with brine
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-a4c08f0c9e4e4d0b9e105ff1aff79008
Source dataset
uspto-grants-2011_10
Patent number
US08039478B2

Reaction notes

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