2,2,3-Tribromopropanal → 3-Bromo-8-iodo-6-nitro-quinoline

HRID 2421533Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2421533
[I:1][C:2]1[CH:8]=[C:7]([N+:9]([O-:11])=[O:10])[CH:6]=[CH:5][C:3]=1[NH2:4].[Br:12][C:13](Br)([CH2:16]Br)[CH:14]=O>C(O)(=O)C>[Br:12][C:13]1[CH:14]=[N:4][C:3]2[C:5]([CH:16]=1)=[CH:6][C:7]([N+:9]([O-:11])=[O:10])=[CH:8][C:2]=2[I:1]

Komponenten

4

Edukt 2

HCID 931082,2,3-TribromopropanalHCID 2226292-Iodo-4-nitroaniline

Produkt 1

HCID 672145383-Bromo-8-iodo-6-nitro-quinoline

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 176Acetic AcidLösungsmittel

Reaktionsbedingungen

Temperatur
110 °C

Versuchsvorschrift

2-Iodo-4-nitroaniline (5.3 g) in acetic acid (40 ml) was treated with 2,2,3 tribromopropanal (5.9 g) and the mixture was heated at 110° C. for 2 h after which it was cooled to room temperature and filtered. The filtered solid was washed with diethyl ether, suspended in water and treated with saturated sodium hydrogen carbonate. Extraction with ethyl acetate, drying over sodium sulphate, filtration and evaporation under reduced pressure gave the desired product, 3-bromo-8-iodo-6-nitro-quinoline, as a yellow solid after chromatography (silica; hexane/ethyl acetate) (M+379).

Aufarbeitung

  1. temperaturewas cooled to room temperature
  2. filtrationfiltered
  3. washThe filtered solid was washed with diethyl ether
  4. additiontreated with saturated sodium hydrogen carbonate
  5. extractionExtraction with ethyl acetate
  6. dry with materialdrying over sodium sulphate, filtration and evaporation under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-08471c38a077483687d36395e1161e86
Quelldatensatz
uspto-grants-2011_06
Patentnummer
US07956188B2

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