4-(Trifluoromethyl)phenylacetonitrile → HCID 57600293, compound

HRID 2368596Notes

Reaction equation

HRID 2368596 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-5a2c18c4ace14a9ead3cbfeef1a503c1
Source dataset
uspto-grants-2014_04
Patent number
US08703783B2

Reaction notes

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