Ethanol → 2-Benzyl-7-bromo-3-methoxyquinoline

HRID 1359418Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1359418
[NH2:1][C:2]1[CH:9]=[C:8]([Br:10])[CH:7]=[CH:6][C:3]=1[CH:4]=O.[CH3:11][O:12][CH2:13][C:14]([CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)=O.[OH-].[K+].C(O)C>O>[CH2:16]([C:14]1[C:13]([O:12][CH3:11])=[CH:4][C:3]2[C:2](=[CH:9][C:8]([Br:10])=[CH:7][CH:6]=2)[N:1]=1)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Komponenten

6

Edukt 4

HCID 702EthanolHCID 14797Potassium HydroxideHCID 117449711-Methoxy-3-phenylpropan-2-oneHCID 179145982-Amino-4-bromobenzaldehyde

Produkt 1

HCID 181823072-Benzyl-7-bromo-3-methoxyquinolineAusbeute 68,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

A mixture of 3.3 g of 2-amino−4-bromobenzaldehyde, 3.3 g of 1-methoxy-3-phenylacetone, an aqueous potassium hydroxide solution (10 g of potassium hydroxide was dissolved in 10 ml of water) and 20 ml of ethanol was heated under stirring at 100° C. for 4 hours in a sealed tube. After cooling as it was, the reaction solution was poured into water and the mixture was extracted with diethyl ether. The organic phase was washed with brine and the solvent was removed. The residue was crystallized from hexane/ethyl acetate, to give 3.7 g of the target compound.

Aufarbeitung

  1. temperatureAfter cooling as it
  2. extractionthe mixture was extracted with diethyl ether
  3. washThe organic phase was washed with brine
  4. customthe solvent was removed
  5. customThe residue was crystallized from hexane/ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-389764ae11ae42609d162513a4b53a03
Quelldatensatz
uspto-grants-2003_07
Patentnummer
US06599917B1

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