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

HRID 1010180Notes

Reaction equation

HRID 1010180 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

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 167845palladium(II) acetateCatalystHCID 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 the reaction 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
  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-54eb256140d049db960e33262dbd78ca
Source dataset
uspto-grants-2011_07
Patent number
US07973160B2

Reaction notes

Loading…