3-Nitrostyrene → HCID 23298101, compound

HRID 1953401Notes

Reaction equation

HRID 1953401 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH:9]=[CH:10][CH:11]=1)[CH:7]=[CH2:8])([O-:3])=[O:2].[C:12]([NH:15][C:16]1[CH:21]=[CH:20][C:19](Br)=[CH:18][N:17]=1)(=[O:14])[CH3:13].C(=O)(O)[O-].[Na+]>[Cl-].C([N+](CCCC)(CCCC)CCCC)CCC.CN(C)C=O.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[C:12]([NH:15][C:16]1[N:17]=[CH:18][C:19](/[CH:8]=[CH:7]/[C:6]2[CH:5]=[C:4]([N+:1]([O-:3])=[O:2])[CH:11]=[CH:10][CH:9]=2)=[CH:20][CH:21]=1)(=[O:14])[CH3:13]

Participants

7

Reactant 3

HCID 685143-NitrostyreneHCID 2930972-Acetamido-5-bromopyridineHCID 516892Sodium Bicarbonate

Product 1

HCID 23298101HCID 23298101, compoundYield 90.3%

Reagents, catalysts & solvents 3

HCID 70681Tetrabutylammonium ChlorideCatalystHCID 167845palladium(II) acetateCatalystHCID 6228DimethylformamideSolvent

Procedure

A mixture of 3-nitrostyrene (7.0 g), 2-acetamido-5-bromopyridine (10.1 g), tetra-n-butylammonium chloride (13.1 g), palladium(II) acetate (0.08 g) and sodium bicarbonate (9.87 g) in N,N-dimethylformamide (70 ml) was stirred at 110pbC. for 6 hours. The reaction mixture was poured into ice-water and precipitated crystals were collected, washed with water and dried to give 3-[(E)-2-(6-acetamido-3-pyridyl)vinyl]nitrobenzene (12.0 g).

Workup

  1. customprecipitated crystals
  2. customwere collected
  3. washwashed with water
  4. customdried

Sources & evidence

ORD record
ord-b2e4fbccb6c34faebd40f2c3c2c38499
Source dataset
uspto-grants-2000_09
Patent number
US06117875

Reaction notes

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