Water → 2-(3-Amino-5-tert-butyl-2-methoxyphenyl)-2-methylpropanenitrile

HRID 243811Notes

Reaction equation

HRID 243811 reaction equation
[C:1]([C:5]1[CH:6]=[C:7]([N+:18]([O-])=O)[C:8]([O:16][CH3:17])=[C:9]([C:11]([CH3:15])([CH3:14])[C:12]#[N:13])[CH:10]=1)([CH3:4])([CH3:3])[CH3:2].[Cl-].[NH4+].O>C(O)C.[Fe]>[NH2:18][C:7]1[C:8]([O:16][CH3:17])=[C:9]([C:11]([CH3:15])([CH3:14])[C:12]#[N:13])[CH:10]=[C:5]([C:1]([CH3:4])([CH3:2])[CH3:3])[CH:6]=1

Participants

6

Reactant 3

HCID 962WaterHCID 25517Ammonium ChlorideHCID 681076692-(5-Tert-butyl-2-methoxy-3-nitrophenyl)-2-methylpropanenitrile

Product 1

HCID 681072452-(3-Amino-5-tert-butyl-2-methoxyphenyl)-2-methylpropanenitrileYield 67%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 702EthanolSolvent

Procedure

To a solution of 2-(5-tert-butyl-2-methoxy-3-nitrophenyl)-2-methylpropanenitrile (0.086 g, 0.311 mmol) in ethanol (3.1 mL), iron (0.087 g, 1.56 mmol), ammonium chloride (0.083 g, 1.56 mmol) and water (1.6 mL) were added, and the mixture was stirred for 3 hours under reflux. The reaction mixture was filtered and washed with ethanol. The obtained filtrate was evaporated under reduced pressure and the residue was dissolved in dichloromethane. After washing this solution with water and then saturated brine, the solution was dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure and the obtained residue was purified by silica gel column chromatography (ethyl acetate/n-hexane=0/100-30/70) to obtain 0.051 g of the captioned compound (67% yield).

Workup

  1. temperatureunder reflux
  2. filtrationThe reaction mixture was filtered
  3. washwashed with ethanol
  4. customThe obtained filtrate was evaporated under reduced pressure
  5. dissolutionthe residue was dissolved in dichloromethane
  6. washAfter washing this solution with water
  7. dry with materialsaturated brine, the solution was dried over anhydrous sodium sulfate
  8. customThe solvent was evaporated under reduced pressure
  9. customthe obtained residue was purified by silica gel column chromatography (ethyl acetate/n-hexane=0/100-30/70)

Sources & evidence

ORD record
ord-cef991bdadcb4d95878b4990acbbc859
Source dataset
uspto-grants-2014_02
Patent number
US08653304B2

Reaction notes

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