1,4-Dioxane → HCID 14998967, compound

HRID 1197667Notes

Reaction equation

HRID 1197667 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([C:10]2[CH:15]=[CH:14][N:13]=[CH:12][C:11]=2[CH2:16][C:17](=O)C=C)[CH:7]=[CH:8][CH:9]=1)([O-:3])=[O:2].[CH3:21]/[C:22](/[NH2:26])=[CH:23]\[C:24]#[N:25].C(=O)([O-])O.[Na+].O1CCO[CH2:34][CH2:33]1>[Cl-].[Zn+2].[Cl-]>[C:24]([C:23]1[CH:10]([C:6]2[CH:7]=[CH:8][CH:9]=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=2)[C:15]([C:14]2[CH:17]=[CH:16][CH:11]=[CH:12][N:13]=2)=[C:33]([CH3:34])[NH:26][C:22]=1[CH3:21])#[N:25]

Participants

6

Reactant 4

HCID 312751,4-DioxaneHCID 516892Sodium BicarbonateHCID 53247203-AminocrotonitrileHCID 67850751HCID 67850751, compound

Product 1

HCID 14998967HCID 14998967, compound

Reagents, catalysts & solvents 1

HCID 3007855ZincchlorideCatalyst

Procedure

A mixuture of 0.536 g (2 mmol) of 4-(3-nitrophenyl)-3-pyridyl-3-butene-2-one, 0.821 g (10 mmol) of 3-aminocrotonitrile, 0.546 g (4 mmol) of zinc chloride, and 1.0 g of Molecular Shieves 4A was added to 1,4-dioxane. This reaction mixture was refluxed with application of heat in an inert atmoshpere for 5 hours. The reaction mixture was then cooled to room temperature and neutralized with a saturated aqueous solution of sodium hydrogencarbonate, followed by extraction with chloroform. The solvents contained in the extract were distilled off and the residue was chromatographed on a silica gel column, whereby the captioned compound was obtained. The yield was 0.59 g (84.6%).

Workup

  1. temperatureThis reaction mixture was refluxed with application
  2. temperatureof heat in an inert atmoshpere for 5 hours
  3. extractionfollowed by extraction with chloroform
  4. distillationwere distilled off
  5. customthe residue was chromatographed on a silica gel column, whereby the captioned compound
  6. customwas obtained

Sources & evidence

ORD record
ord-a4d5247553a548f0832953537be51b96
Source dataset
uspto-grants-1994_01
Patent number
US05276150

Reaction notes

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