Benzaldehyde → 2-Amino-2-phenylacetonitrile

HRID 34134Notes

Reaction equation

HRID 34134 reaction equation
[C-:1]#[N:2].[Na+].[Cl-].[NH4+:5].[CH:6](=O)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1>CO>[NH2:5][CH:6]([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)[C:1]#[N:2]

Participants

5

Reactant 3

HCID 240BenzaldehydeHCID 8929Sodium CyanideHCID 25517Ammonium Chloride2×

Product 1

HCID 408382-Amino-2-phenylacetonitrileYield 35.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a 0.3 ml aqueous solution of 46 mg of sodium cyanide and 55 mg of ammonium chloride was added a solution of 100 mg of benzaldehyde in 0.3 ml of methanol, and the resulting mixture was stirred at room temperature for 5 hours. After adding aqueous solution of ammonium chloride to the reaction mixture, it was extracted with ethyl acetate twice. The organic layer was washed successively with a saturated aqueous solution of ammonium chloride and saturated brine, dried over anhydrous magnesium sulfate, and the solvent was evaporated. Then, the crude product was purified and separated by LC-MS, to give 44.2 mg of the title compound as colorless crystals.

Workup

  1. extractionwas extracted with ethyl acetate twice
  2. washThe organic layer was washed successively with a saturated aqueous solution of ammonium chloride and saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customthe solvent was evaporated
  5. customThen, the crude product was purified
  6. customseparated by LC-MS

Sources & evidence

ORD record
ord-dd905301c00e4bb5a01b323e2231ebf6
Source dataset
uspto-grants-2008_09
Patent number
US07429609B2

Reaction notes

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