Ethylamine → 6-(2-Nitro-1-propenyl)imidazo[1,2-a]pyridine

HRID 414321

Reaktionsgleichung

Reaktionsgleichung von HRID 414321
[N:1]1[CH:2]=[CH:3][N:4]2[CH:9]=[C:8]([CH:10]=O)[CH:7]=[CH:6][C:5]=12.[N+:12]([CH2:15][CH3:16])([O-:14])=[O:13].C(N)C>C(O)C.C(N)CCC>[N+:12]([C:15]([CH3:16])=[CH:10][C:8]1[CH:7]=[CH:6][C:5]2[N:4]([CH:3]=[CH:2][N:1]=2)[CH:9]=1)([O-:14])=[O:13]

Komponenten

6

Edukt 3

HCID 6341EthylamineHCID 6587NitroethaneHCID 7164582Imidazo[1,2-a]pyridine-6-carbaldehyde

Produkt 1

HCID 539155686-(2-Nitro-1-propenyl)imidazo[1,2-a]pyridineAusbeute 11,9 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8007ButylamineKatalysatorHCID 702EthanolLösungsmittel

Versuchsvorschrift

In 40 ml of ethanol, 6.9 g of 6-imidazo[1,2-a]pyridinecarbaldehyde was stirred under reflux for 14 hours, together with 10.6 g of nitroethane and 30 drops of n-butyl amine. Then, a small quantity of ethyl amine was added thereto and the mixture was stirred under reflux for further 18 hours. After insoluble matter was removed by filtration upon heating, 50 ml of ethanol and 150 ml of ether were further added to remove insoluble matter by filtration. The solvent was removed by distillation under reduced pressure and the residue was recrystallized twice from ethanol to obtain 1.14 g of 6-(2-nitro-1-propenyl)imidazo[1,2-a]pyridine.

Aufarbeitung

  1. temperatureunder reflux for further 18 hours
  2. customAfter insoluble matter was removed by filtration
  3. temperatureupon heating
  4. addition50 ml of ethanol and 150 ml of ether were further added
  5. customto remove insoluble matter
  6. filtrationby filtration
  7. customThe solvent was removed by distillation under reduced pressure
  8. customthe residue was recrystallized twice from ethanol

Quellen und Nachweise

ORD-Eintrag
ord-b67346cabdc447b4ae4a5cb1e2f69ef5
Quelldatensatz
uspto-grants-1988_12
Patentnummer
US04791202

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