3-(2-Cyanoethoxymethyl)-2-nitrotoluene → 2-(3-Aminopropoxymethyl)-6-methylaniline

HRID 1906141Notes

Reaction equation

HRID 1906141 reaction equation
[C:1]([CH2:3][CH2:4][O:5][CH2:6][C:7]1[C:8]([N+:14]([O-])=O)=[C:9]([CH3:13])[CH:10]=[CH:11][CH:12]=1)#[N:2]>C(O)(=O)C.[Pt](=O)=O>[NH2:2][CH2:1][CH2:3][CH2:4][O:5][CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([CH3:13])[C:8]=1[NH2:14]

Participants

4

Reactant 1

HCID 202126833-(2-Cyanoethoxymethyl)-2-nitrotoluene

Product 1

HCID 202126812-(3-Aminopropoxymethyl)-6-methylanilineYield 30%

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalystHCID 176Acetic AcidSolvent

Procedure

A solution of 12 g (55 mMol) of the nitro compound (2) in 140 ml of glacial acetic acid was combined with 550 mg of platinum dioxide (PtO2) and shaken at room temperature under a hydrogen atmosphere of 50 pounds per square inch (psi) for 6 hours. It was then filtered to remove the catalyst and the solvent was evaporated under reduced pressure. The residue was dissolved in 100 ml of n-butanol and the solution washed twice with 50 ml of saturated aqueous sodium bicarbonate solution. The aqueous washes were combined and extracted two 75 ml portions of n-butanol. The combined butanol extracts were combined, dried over anhydrous sodium sulfate (Na2SO4), and evaporated. The oily residue was purified on a preparative liquid chromatograph using silica gel as the adsorbent and eluting with 40:10:1 (v/v/v) chloroform (CHCl3):methanol:conc. ammonium hydroxide. This yielded 3.15 g (30% yield) of 2-(3-aminopropoxymethyl)-6-methylaniline (3) as an oil.

Workup

  1. filtrationIt was then filtered
  2. customto remove the catalyst
  3. customthe solvent was evaporated under reduced pressure
  4. dissolutionThe residue was dissolved in 100 ml of n-butanol
  5. washthe solution washed twice with 50 ml of saturated aqueous sodium bicarbonate solution
  6. extractionextracted two 75 ml portions of n-butanol
  7. dry with materialdried over anhydrous sodium sulfate (Na2SO4)
  8. customevaporated
  9. customThe oily residue was purified on a preparative liquid chromatograph
  10. washeluting with 40:10:1 (v/v/v) chloroform (CHCl3)

Sources & evidence

ORD record
ord-a42fee8867de441b81938fd9c4e89d7f
Source dataset
uspto-grants-1987_03
Patent number
US04650771

Reaction notes

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