Dimethyl malonate → Dimethyl (alpha-amino-3-nitrobenzylidene)malonate

HRID 981151

Reaktionsgleichung

Reaktionsgleichung von HRID 981151
[C:1]([O:8][CH3:9])(=[O:7])[CH2:2][C:3]([O:5][CH3:6])=[O:4].[N+:10]([C:13]1[CH:14]=[C:15]([CH:18]=[CH:19][CH:20]=1)[C:16]#[N:17])([O-:12])=[O:11]>ClCCCl>[NH2:17][C:16](=[C:2]([C:1]([O:8][CH3:9])=[O:7])[C:3]([O:5][CH3:6])=[O:4])[C:15]1[CH:18]=[CH:19][CH:20]=[C:13]([N+:10]([O-:12])=[O:11])[CH:14]=1

Komponenten

4

Edukt 2

HCID 7943Dimethyl malonateHCID 120793-Nitrobenzonitrile

Produkt 1

HCID 9970879Dimethyl (alpha-amino-3-nitrobenzylidene)malonateAusbeute 65,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 111,2-DichloroethaneLösungsmittel

Versuchsvorschrift

To a mixture of dimethyl malonate (100 g) and 3-nitrobenzonitrile (112 g) in 1,2-dichloroethane (500 ml) was added stannic chloride (177 g) at once with a syringe and refluxed for 1 hour with stirring. The white precipitates were collected by filtration, dissolved in a mixture of acetone (2 l) and water (2 l) and adjusted to pH 9.0 with 20% aqueous sodium hydroxide. The resulting white solid was filtered off, and the filtrate was extracted with methylene chloride (2 l). The extract was washed with saturated aqueous sodium chloride, dried over magnesium sulfate and evaporated in vacuo. The resulting precipitates were recrystallized from a mixture of diethyl ether and methylene chloride to give dimethyl (α-amino-3-nitrobenzylidene)malonate (139.5 g).

Aufarbeitung

  1. temperaturerefluxed for 1 hour
  2. customThe white precipitates
  3. filtrationwere collected by filtration
  4. dissolutiondissolved in a mixture of acetone (2 l) and water (2 l)
  5. filtrationThe resulting white solid was filtered off
  6. extractionthe filtrate was extracted with methylene chloride (2 l)
  7. washThe extract was washed with saturated aqueous sodium chloride
  8. dry with materialdried over magnesium sulfate
  9. customevaporated in vacuo
  10. customThe resulting precipitates
  11. customwere recrystallized from a mixture of diethyl ether and methylene chloride

Quellen und Nachweise

ORD-Eintrag
ord-1c7c93751cc44407acb48d0aa815c7d4
Quelldatensatz
uspto-grants-1991_02
Patentnummer
US04990507

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