Ammonia → alpha-Amino-1,3-benzodioxole-5-acetonitrile

HRID 382896

Reaction equation

HRID 382896 reaction equation
[CH:1]1[C:6]([CH:7]=O)=[CH:5][C:4]2[O:9][CH2:10][O:11][C:3]=2[CH:2]=1.[NH3:12].[NH4+:13].[Cl-].[C-:15]#N.[K+].[O-]S([O-])(=O)=O.[Mg+2]>C1COCC1>[NH2:12][CH:7]([C:6]1[CH:1]=[CH:2][C:3]2[O:11][CH2:10][O:9][C:4]=2[CH:5]=1)[C:15]#[N:13]

Participants

7

Reactant 5

HCID 222AmmoniaHCID 8438PiperonalHCID 9032Potassium CyanideHCID 24083Sulfuric acid magnesium salt (1:1)HCID 25517Ammonium Chloride

Product 1

HCID 4405684alpha-Amino-1,3-benzodioxole-5-acetonitrile

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Piperonal (6.00 g) is dissolved in THF (25 mL) and aq. NH3 (58%, 4.2 mL), NH4Cl (3.3 g) and KCN (3.9 g) are added. The mixture is stirred efficiently for 24 h. MgSO4 is added and the mixture stirred for 30 min., filtered and washed with THF The filtrate is evaporated under reduced pressure and the residue purified by FC (Et2O/petrol ether 1:2,→2:1,→Et2O). Aminonitrile W-99 is obtained as a brown, unstable oil (2.87 g). The hydrochloride salt is precipitated from sat. HCl/Et2O for analytical purposes.

Workup

  1. stirringthe mixture stirred for 30 min.
  2. filtrationfiltered
  3. washwashed with THF The filtrate
  4. customis evaporated under reduced pressure
  5. customthe residue purified by FC (Et2O/petrol ether 1:2,→2:1,→Et2O)

Sources & evidence

ORD record
ord-ed0297be245e41a784d8d777021bd689
Source dataset
uspto-grants-2001_10
Patent number
US06310211B1

Linked notes

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