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Acetone → Ethyl(E)-3-[2-amino-4-(4-nitrophenoxy)-3-pyridyl]-2-propenoate

HRID 853315
Notes
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Reaction equation

HRID 853315 reaction equation
I[C:2]1[C:3]([NH2:18])=[N:4][CH:5]=[CH:6][C:7]=1[O:8][C:9]1[CH:14]=[CH:13][C:12]([N+:15]([O-:17])=[O:16])=[CH:11][CH:10]=1.[C:19]([O:23][CH2:24][CH3:25])(=[O:22])[CH:20]=[CH2:21].C(N(CCCC)CCCC)CCC.CC(C)=O>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.O>[NH2:18][C:3]1[C:2](/[CH:21]=[CH:20]/[C:19]([O:23][CH2:24][CH3:25])=[O:22])=[C:7]([O:8][C:9]2[CH:14]=[CH:13][C:12]([N+:15]([O-:17])=[O:16])=[CH:11][CH:10]=2)[CH:6]=[CH:5][N:4]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 180AcetoneHCID 7622TributylamineHCID 8821Ethyl AcrylateHCID 229363343-Iodo-4-(4-nitrophenoxy)-2-pyridinamine

Product 1

HCID 58931221Ethyl(E)-3-[2-amino-4-(4-nitrophenoxy)-3-pyridyl]-2-propenoate

Reagents, catalysts & solvents 2

HCID 167845
palladium(II) acetate
Catalyst
HCID 962WaterSolvent

Procedure

3-Iodo-4-(4-nitrophenoxy)-2-pyridinamine (500 mg), ethyl acrylate (0.3 ml), palladium (II) acetate (30 mg), tributylamine (0.66 ml) and dimethylformaldehyde (5 ml) were stirred at 130° C. for 20 minutes. After returning the reaction solution to room temperature, water was added and extraction was performed with ethyl acetate. NH type silica gel was added to the extract, the solvent was distilled off under reduced pressure, and there action product was adsorbed onto the silica gel. The silica gel was charged into a dry column packed with NH type silica gel, and column purification was performed (hexane:ethyl acetate=3:1). The solvent was distilled off under reduced pressure to obtain 330 mg of the target substance as a yellow oil.

Workup

  1. customto room temperature
  2. extractionextraction
  3. additionNH type silica gel was added to the extract
  4. distillationthe solvent was distilled off under reduced pressure, and there action product
  5. additionThe silica gel was charged into a dry column
  6. custompacked with NH type silica gel, and column purification
  7. distillationThe solvent was distilled off under reduced pressure
  8. customto obtain 330 mg of the target substance as a yellow oil

Sources & evidence

ORD record
ord-f9e87ea063ae49f283e54ae6276b9716
Source dataset
uspto-grants-2007_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07253286B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes