4-(Trifluoromethyl)phenylacetonitrile → HCID 57600293, compound

HRID 1787797Notes

Reaction equation

HRID 1787797 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-d51dd7d15d5e4298aa7b7e63bbb7ea18
Source dataset
uspto-grants-2009_03
Patent number
US07511050B2

Reaction notes

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