Water → 6-Hydroxyquinoline-5-carbaldehyde

HRID 66598

Reaktionsgleichung

Reaktionsgleichung von HRID 66598
[OH-:1].[Na+].[OH2:3].O[C:5]1[CH:6]=[C:7]2[C:12](=[CH:13][CH:14]=1)[N:11]=[CH:10][CH:9]=[CH:8]2.[CH:15](Cl)(Cl)Cl>>[OH:1][C:5]1[CH:14]=[CH:13][C:12]2[N:11]=[CH:10][CH:9]=[CH:8][C:7]=2[C:6]=1[CH:15]=[O:3]

Komponenten

5

Edukt 4

HCID 962WaterHCID 6212Chloroform2×HCID 113746-HydroxyquinolineHCID 14798Sodium Hydroxide

Produkt 1

HCID 135600936-Hydroxyquinoline-5-carbaldehyde

Reaktionsbedingungen

Temperatur
90 °C

Versuchsvorschrift

Sodium hydroxide (25 g.) was dissolved in 35 ml. of water with cooling, 6-hydroxyquinoline (5 g.) in 15 ml. of chloroform was added and the reaction mixture heated to reflux (about 90° C.) for 12 hours, during which two further 15 ml. portions of chloroform were added--one after 2 hours and the other after 6 hours. The reaction mixture was cooled and crude product recovered by filtration. The crude was dissolved in 125 ml. of hot water treated with activated carbon, filtered hot, cooled and acidified with acetic acid and filtered to yield title product [2.5 g.; m.p 136°-137° C.; m/e 173; pnmr/CDCl3 shows aldehyde proton at 10.5 ppm and aromatic protons at 7.2-9.4 ppm⟧

Aufarbeitung

  1. temperaturethe reaction mixture heated
  2. waitthe other after 6 hours
  3. temperatureThe reaction mixture was cooled
  4. filtrationcrude product recovered by filtration
  5. dissolutionThe crude was dissolved in 125 ml
  6. additionof hot water treated with activated carbon
  7. filtrationfiltered hot
  8. temperaturecooled
  9. filtrationfiltered

Quellen und Nachweise

ORD-Eintrag
ord-12a8023b7b894ac3bb091ca882f9c9db
Quelldatensatz
uspto-grants-1982_08
Patentnummer
US04342771

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