Ethanol → 2-Amino-2-methyl-4-(2-trifluoromethylphenyl)butyronitrile

HRID 9929Notes

Reaction equation

HRID 9929 reaction equation
[F:1][C:2]([F:15])([F:14])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[CH2:9][CH2:10]C(=O)C.[C-:16]#[N:17].[Na+].[Cl-].[NH4+:20].[CH2:21](O)[CH3:22]>N>[NH2:20][C:21]([CH3:22])([CH2:10][CH2:9][C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][C:3]=1[C:2]([F:15])([F:14])[F:1])[C:16]#[N:17]

Participants

6

Reactant 4

HCID 702EthanolHCID 8929Sodium CyanideHCID 25517Ammonium ChlorideHCID 117460214-[2-(Trifluoromethyl)phenyl]butan-2-one

Product 1

HCID 112187182-Amino-2-methyl-4-(2-trifluoromethylphenyl)butyronitrile

Reagents, catalysts & solvents 1

HCID 222AmmoniaSolvent

Procedure

1.5 g of 4-(2-trifluoromethylphenyl)butan-2-one, 0.41 g of sodium cyanide and 0.56 g of ammonium chloride are dissolved in 77 ml of a 2M solution of ammonia in ethanol and the mixture is stirred at ambient temperature for 7 h. The mixture is subsequently concentrated under reduced pressure and the residue is redissolved in ethyl acetate and washed with water and three times with saturated sodium chloride solution. The organic phase is separated, dried with magnesium sulfate and evaporated under reduced pressure. After purifying the residue by flash chromatography, the title compound is thus obtained.

Workup

  1. concentrationThe mixture is subsequently concentrated under reduced pressure
  2. dissolutionthe residue is redissolved in ethyl acetate
  3. washwashed with water and three times with saturated sodium chloride solution
  4. customThe organic phase is separated
  5. dry with materialdried with magnesium sulfate
  6. customevaporated under reduced pressure
  7. customAfter purifying the residue by flash chromatography

Sources & evidence

ORD record
ord-f7bffe1edf2743528fa2a6dad5094133
Source dataset
uspto-grants-2006_08
Patent number
US07091371B2

Reaction notes

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