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

HRID 1381674

Reaktionsgleichung

Reaktionsgleichung von HRID 1381674
[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 matters were removed by filtration upon heating, 50 ml of ethanol and 150 ml of ether were further added to remove insoluble matters 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 matters were removed by filtration
  3. temperatureupon heating
  4. addition50 ml of ethanol and 150 ml of ether were further added
  5. customto remove insoluble matters
  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-8a9534cb3d594672809d311345e469c8
Quelldatensatz
uspto-grants-1989_02
Patentnummer
US04803276

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