Trifluoroacetic acid → (4-Amino-3-methylphenyl)acetonitrile

HRID 1861963Notes

Reaction equation

HRID 1861963 reaction equation
C(OC(=O)[NH:7][C:8]1[CH:13]=[CH:12][C:11]([CH2:14][C:15]#[N:16])=[CH:10][C:9]=1[CH3:17])(C)(C)C.FC(F)(F)C(O)=O.C(=O)(O)[O-].[Na+]>C(Cl)Cl>[C:15]([CH2:14][C:11]1[CH:12]=[CH:13][C:8]([NH2:7])=[C:9]([CH3:17])[CH:10]=1)#[N:16]

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 516892Sodium BicarbonateHCID 53943733tert-butyl N-[4-(cyanomethyl)-2-methylphenyl]carbamate

Product 1

HCID 18621900(4-Amino-3-methylphenyl)acetonitrileYield 70%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The compound (1.16 g) obtained in Example 520 was dissolved in methylene chloride (15 ml); to the solution, trifluoroacetic acid (4 ml) was added and the mixture was stirred at room temperature for 1 h. A saturated aqueous sodium bicarbonate solution was added to the reaction mixture, which was extracted with methylene chloride. The organic layer was dried with anhydrous sodium sulfate and the solvent was distilled off under reduced pressure. The resulting residue was purified by silica gel column chromatography (eluent, n-hexane:ethyl acetate=3:1) to give 480.5 mg of the titled compound (yield, 70%).

Workup

  1. extractionwas extracted with methylene chloride
  2. dry with materialThe organic layer was dried with anhydrous sodium sulfate
  3. distillationthe solvent was distilled off under reduced pressure
  4. customThe resulting residue was purified by silica gel column chromatography (eluent, n-hexane:ethyl acetate=3:1)

Sources & evidence

ORD record
ord-e5029b433c0e4aa3b10065e27930ceab
Source dataset
uspto-grants-2003_03
Patent number
US06534546B1

Reaction notes

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