Nitromethane → 2-(Benzyloxy)-5-[(E)-2-nitroethenyl]pyridine

HRID 1694240Notes

Reaction equation

HRID 1694240 reaction equation
[CH2:1]([O:8][C:9]1[N:14]=[CH:13][C:12]([CH:15]=O)=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[N+:17]([CH3:20])([O-:19])=[O:18].C([O-])(=O)C.[NH4+]>C(O)(=O)C>[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][C:12](/[CH:15]=[CH:20]/[N+:17]([O-:19])=[O:18])=[CH:13][N:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 6375NitromethaneHCID 517165Ammonium AcetateHCID 211022056-(Benzyloxy)nicotinaldehyde

Product 1

HCID 566051462-(Benzyloxy)-5-[(E)-2-nitroethenyl]pyridine

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of 6-benzyloxy-pyridine-3-carbaldehyde described in Manufacturing Example 231-1-2 (36.8 g, 173 mmol) in acetic acid (100 mL) were added nitromethane (52.8 g, 865 mmol) and ammonium acetate (26.7 g, 346 mmol) under nitrogen atmosphere at room temperature, which was stirred for 2.5 hours at 100° C. The reaction mixture was partitioned into water and ethyl acetate. The organic layer was washed with water and saturated aqueous sodium chloride, dried over anhydrous magnesium sulfate, and then filtered. The filtrate was concentrated under a reduced pressure to obtain the title compound (44.0 g) as a crude 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. filtrationfiltered
  5. concentrationThe filtrate was concentrated under a reduced pressure

Sources & evidence

ORD record
ord-00ff5a84c81b4cb5bd7db40f254ea6e5
Source dataset
uspto-grants-2012_04
Patent number
US08158657B2

Reaction notes

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