Nitromethane → 2-Methyl-6-(4-((E)-2-nitro-vinyl)-benzyloxy)-pyridine

HRID 1690912

Reaktionsgleichung

Reaktionsgleichung von HRID 1690912
[CH3:1][C:2]1[N:7]=[C:6]([O:8][CH2:9][C:10]2[CH:17]=[CH:16][C:13]([CH:14]=O)=[CH:12][CH:11]=2)[CH:5]=[CH:4][CH:3]=1.[N+:18]([CH3:21])([O-:20])=[O:19].C([O-])(=O)C.[NH4+]>C(O)(=O)C>[CH3:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]([O:8][CH2:9][C:10]2[CH:17]=[CH:16][C:13](/[CH:14]=[CH:21]/[N+:18]([O-:20])=[O:19])=[CH:12][CH:11]=2)[N:7]=1

Komponenten

5

Edukt 3

HCID 6375NitromethaneHCID 517165Ammonium AcetateHCID 592551484-(6-Methyl-pyridin-2-yloxymethyl)-benzaldehyde

Produkt 1

HCID 592553682-Methyl-6-(4-((E)-2-nitro-vinyl)-benzyloxy)-pyridineAusbeute 110 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 176Acetic AcidLösungsmittel

Reaktionsbedingungen

Temperatur
110 °C

Versuchsvorschrift

To a solution of 4-(6-methyl-pyridin-2-yloxymethyl)-benzaldehyde (4.19 g, 18.5 mmol) described in Manufacturing Example 3-1-2 in acetic acid (30 mL) were added nitromethane (5.65 g, 92.6 mmol) and ammonium acetate (2.85 g, 37.0 mmol) under nitrogen atmosphere, which was stirred for 3 hours at 110° 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 evaporated under a reduced pressure to obtain the title compound (5.50 g) as a crude product.

Aufarbeitung

  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. customthe solvent was evaporated under a reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-086e68730a474775a518306be97f91e6
Quelldatensatz
uspto-grants-2012_04
Patentnummer
US08153662B2

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