Ethyl Acetate → [3-(2-Methyl-1,3-dioxolan-2-yl)phenyl]methanamine

HRID 1734010Notes

Reaction equation

HRID 1734010 reaction equation
[CH3:1][C:2]1([C:7]2[CH:8]=[C:9]([CH:12]=[CH:13][CH:14]=2)[C:10]#[N:11])[O:6][CH2:5][CH2:4][O:3]1.[H-].[Al+3].[Li+].[H-].[H-].[H-].C(OCC)(=O)C>O1CCCC1>[CH3:1][C:2]1([C:7]2[CH:8]=[C:9]([CH:12]=[CH:13][CH:14]=2)[CH2:10][NH2:11])[O:3][CH2:4][CH2:5][O:6]1

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 105595463-(2-Methyl-1,3-dioxolan-2-yl)benzonitrileHCID 21226445Aluminium lithium hydride

Product 1

HCID 10726441[3-(2-Methyl-1,3-dioxolan-2-yl)phenyl]methanamineYield 85.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 3-(2-methyl-1,3-dioxolan-2-yl)benzonitrile (65.6 g) in tetrahydrofuran (400 ml) was added to a suspension of lithium aluminum hydride (26.3 g) in tetrahydrofuran (400 ml) with cooling on an ice-water bath under nitrogen stream for 1 hour. The mixture was stirred at room temperature for 2 hours. Ethyl acetate (200 ml) was added slowly with cooling on an ice bath and then ice-water (200 ml) was added very slowly with cooling on an ice bath. The resulting precipitate was removed by filtration. The solvent was removed under reduced pressure. Chloroform (300 ml) was added to the residue. The mixture was washed with water (100 ml) and then dried with magnesium sulfate. The solvent was removed under reduced pressure to afford 3-(2-methyl-1,3-dioxolan-2-yl)benzylamine (57.2 g) (oil).

Workup

  1. temperaturewith cooling on an ice-water bath under nitrogen stream for 1 hour
  2. temperaturewith cooling on an ice bath
  3. temperaturewith cooling on an ice bath
  4. customThe resulting precipitate was removed by filtration
  5. customThe solvent was removed under reduced pressure
  6. additionChloroform (300 ml) was added to the residue
  7. washThe mixture was washed with water (100 ml)
  8. dry with materialdried with magnesium sulfate
  9. customThe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-540ccbe5c5e8424eafe66435e366c91f
Source dataset
uspto-grants-1996_07
Patent number
US05532258

Reaction notes

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