Sodium Bicarbonate → HCID 14998980, compound

HRID 1197668Notes

Reaction equation

HRID 1197668 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9](=[CH:13][C:14]1[CH:19]=[CH:18][CH:17]=[C:16]([N+:20]([O-:22])=[O:21])[CH:15]=1)[C:10](=O)[CH3:11].[NH2:23]/[C:24](/[CH3:30])=[CH:25]\[C:26]([O:28][CH3:29])=[O:27].C(=O)([O-])O.[Na+]>[Cl-].[Zn+2].[Cl-].O1CCOCC1>[CH3:30][C:24]1[NH:23][C:10]([CH3:11])=[C:9]([C:4]2[CH:5]=[CH:6][CH:7]=[CH:8][C:3]=2[O:2][CH3:1])[CH:13]([C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([N+:20]([O-:22])=[O:21])[CH:15]=2)[C:25]=1[C:26]([O:28][CH3:29])=[O:27]

Participants

6

Reactant 3

HCID 516892Sodium BicarbonateHCID 643918Methyl 3-aminocrotonateHCID 54193274HCID 54193274, compound

Product 1

HCID 14998980HCID 14998980, compound

Reagents, catalysts & solvents 2

HCID 3007855ZincchlorideCatalystHCID 312751,4-DioxaneSolvent

Procedure

A mixuture of 297 mg (1 mmol) of 3-(2-methoxyphenyl)-4-(3-nitrophenyl)-3-butene-2-one, 575 mg (5 mmol) of methyl 3-aminocrotonate, 273 mg (2 mmol) of zinc chloride, and 500 mg 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 216 mg (55%).

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-c23261b40353428b8aced93384272420
Source dataset
uspto-grants-1994_01
Patent number
US05276150

Reaction notes

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