Ammonia → beta-Amino-2-chlorocinnamonitrile

HRID 2051623Notes

Reaction equation

HRID 2051623 reaction equation
N.[Na].[C:3](#[N:5])[CH3:4].[Cl:6][C:7]1[CH:14]=[CH:13][CH:12]=[CH:11][C:8]=1[C:9]#[N:10]>O1CCCC1.C(OCC)C>[NH2:10][C:9]([C:8]1[CH:11]=[CH:12][CH:13]=[CH:14][C:7]=1[Cl:6])=[CH:4][C:3]#[N:5]

Participants

7

Reactant 4

HCID 222Ammonia2×HCID 6342AcetonitrileHCID 133912-ChlorobenzonitrileHCID 5360545Sodium2×

Product 1

HCID 70509051beta-Amino-2-chlorocinnamonitrile

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

A 150 ml. portion of ammonia is condensed in a reaction flask and a small piece of sodium is added. The blue color is discharged by the addition of ferric chloride and 3.22 g. of sodium are added. After the color is discharged, 5.75 ml. of acetonitrile in 10 ml. of diethyl ether are added. The reaction is cooled in a dry ice-acetone bath and 13.3 g. of 2-chlorobenzonitrile in 25 ml. of tetrahydrofuran are added dropwise. The ammonia is allowed to evaporate, the solvent is blown off with nitrogen and water is added. The mixture is extracted with methylene chloride. The organic extracts are dried over sodium sulfate and filtered through Magnesol®. The filtrate is evaporated with the addition of hexanes giving β-amino-2-chlorocinnamonitrile as a white crystalline solid.

Workup

  1. customcondensed in a reaction flask
  2. temperatureThe reaction is cooled in a dry ice-acetone bath
  3. customto evaporate
  4. additionis added
  5. extractionThe mixture is extracted with methylene chloride
  6. dry with materialThe organic extracts are dried over sodium sulfate
  7. filtrationfiltered through Magnesol®
  8. customThe filtrate is evaporated with the addition of hexanes

Sources & evidence

ORD record
ord-ced20f88816445b2a90138d6178f7a51
Source dataset
uspto-grants-1980_01
Patent number
US04181677

Reaction notes

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