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

HRID 1069537Notes

Reaction equation

HRID 1069537 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
  4. customThe filtrate is evaporated under reduced pressure
  5. customthe residue purified by FC (Et2O/petrol ether 1:2,→2:1,→Et2O)

Sources & evidence

ORD record
ord-838d4b9c67e147af8b79c2c98eb041ba
Source dataset
uspto-grants-2001_06
Patent number
US06252080B1

Reaction notes

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