Ethylenediamine → 4-hydroxy-3-[(Z)-N-[(2-methylpropan-2-yl)oxy]-C-pyridin-2-ylcarbonimidoyl]benzonitrile

HRID 862100Notes

Reaction equation

HRID 862100 reaction equation
[C:1]([O:5]/[N:6]=[C:7](\[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][N:17]=1)/[C:8]1[CH:13]=[C:12](Br)[CH:11]=[CH:10][C:9]=1[OH:15])([CH3:4])([CH3:3])[CH3:2].C(N)[CH2:23][NH2:24]>CN(C=O)C.O>[C:1]([O:5]/[N:6]=[C:7](\[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][N:17]=1)/[C:8]1[CH:13]=[C:12]([C:23]#[N:24])[CH:11]=[CH:10][C:9]=1[OH:15])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 2

HCID 3301EthylenediamineHCID 1364637264-bromo-2-[(Z)-N-[(2-methylpropan-2-yl)oxy]-C-pyridin-2-ylcarbonimidoyl]phenol

Product 1

HCID 1364637874-hydroxy-3-[(Z)-N-[(2-methylpropan-2-yl)oxy]-C-pyridin-2-ylcarbonimidoyl]benzonitrile

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

(Z)-2-(5-bromo-2-hydroxybenzoyl)pyridine O-t-butyloxime (12.7 g) was dissolved in DMF (100 ml). To the solution was added cuprous cyanide (4.64 g), and the mixture was heated, under argon atmosphere, for 3 hours under reflux. To the reaction mixture was added a solution of ethylenediamine (30 ml) in water (20 ml). The mixture was stirred for 30 minutes at room temperature, followed by extraction with ethyl acetate. The organic layer was dried (anhydrous magnesium sulfate), then the solvent was distilled off. The residue was purified by means of a silica gel column chromatography, eluting with ethyl acetate/hexane, to give (Z)-2-(5-cyano-2-hydroxybenzoyl)pyridine O-t-butyloxime (4.31 g) (Compound 76).

Workup

  1. temperaturethe mixture was heated, under argon atmosphere, for 3 hours
  2. temperatureunder reflux
  3. extractionfollowed by extraction with ethyl acetate
  4. dry with materialThe organic layer was dried (anhydrous magnesium sulfate)
  5. distillationthe solvent was distilled off
  6. customThe residue was purified by means of a silica gel column chromatography
  7. washeluting with ethyl acetate/hexane

Sources & evidence

ORD record
ord-2671fda9577d4aed8dbe77c443579a8f
Source dataset
uspto-grants-1998_02
Patent number
US05716971

Reaction notes

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