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

HRID 77806

Reaktionsgleichung

Reaktionsgleichung von HRID 77806
[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-8d3d40763f0c4de1a07f9332ef3d77f1
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08841327B2

Verknüpfte Notizen

Wird geladen…