Nitromethane → 4-(2-Pyridin-2-yl-ethyl)-((E)-2-nitrovinyl)-benzene

HRID 1694022Notes

Reaction equation

HRID 1694022 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[CH2:7][CH2:8][C:9]1[CH:16]=[CH:15][C:12]([CH:13]=O)=[CH:11][CH:10]=1.[N+:17]([CH3:20])([O-:19])=[O:18].C([O-])(=O)C.[NH4+]>C(O)(=O)C>[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[CH2:7][CH2:8][C:9]1[CH:16]=[CH:15][C:12](/[CH:13]=[CH:20]/[N+:17]([O-:19])=[O:18])=[CH:11][CH:10]=1

Participants

5

Reactant 3

HCID 6375NitromethaneHCID 517165Ammonium AcetateHCID 59255317HCID 59255317, compound

Product 1

HCID 592553604-(2-Pyridin-2-yl-ethyl)-((E)-2-nitrovinyl)-benzeneYield 91.2%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
120 °C

Procedure

To an acetic acid (30 mL) solution of 4-(2-pyridin-2-yl-ethyl)benzaldehyde (2.57 g, 12.2 mmol) described in Manufacturing Example 93-1-5 were added nitromethane (7.45 g, 122 mmol) and ammonium acetate (1.88 g, 24.4 mmol) under nitrogen atmosphere at room temperature, which was stirred for 3 hours at 120° C. The reaction mixture was partitioned into water and ethyl acetate. The organic layer was washed with water and saturated aqueous sodium chloride and dried over anhydrous magnesium sulfate, and the solvent was evaporation under a reduced pressure to obtain the title compound (2.83 g, 91%) as a raw product.

Workup

  1. customThe reaction mixture was partitioned into water and ethyl acetate
  2. washThe organic layer was washed with water and saturated aqueous sodium chloride
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customevaporation under a reduced pressure

Sources & evidence

ORD record
ord-25348940eedb49cb9d07e6c3d8194504
Source dataset
uspto-grants-2012_04
Patent number
US08158657B2

Reaction notes

Loading…