Hydrochloric Acid → 6-Hydroxy-4-oxo-1-propionyl-1,2,3,4-tetrahydroquinoline

HRID 653123Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 653123
C[O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[N:9]([C:13](=[O:16])[CH2:14][CH3:15])[CH2:8][CH2:7][C:6]2=[O:17].[Cl-].[Al+3].[Cl-].[Cl-].Cl>C1C=CC=CC=1>[OH:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[N:9]([C:13](=[O:16])[CH2:14][CH3:15])[CH2:8][CH2:7][C:6]2=[O:17]

Komponenten

5

Edukt 3

HCID 313Hydrochloric AcidHCID 6451240Aluminum(III) ChlorideHCID 145014416-Methoxy-4-oxo-1-propionyl-1,2,3,4-tetrahydroquinoline

Produkt 1

HCID 212948076-Hydroxy-4-oxo-1-propionyl-1,2,3,4-tetrahydroquinolineAusbeute 82,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 241BenzeneLösungsmittel

Versuchsvorschrift

A mixture of 6-methoxy-4-oxo-1-propionyl-1,2,3,4-tetrahydroquinoline (1.957 g) and aluminum chloride (3.359 g) in benzene (42 ml) was heated at 60° to 65° with stirring for 4 hours. To the aluminum chloride complex was added a mixture of crushed ice and 10% hydrochloric acid and extracted with ethyl acetate. The extract was washed with water, dried over magnesium sulfate, and evaporated in vacuo. The residue was purified by column chromatography on silica gel (30 g) with a mixture of chloroform and methanol (50:1 to 10:1) as an eluent. The eluates were evaporated in vacuo to give 6-hydroxy-4-oxo-1-propionyl-1,2,3,4-tetrahydroquinoline (1.52 g).

Aufarbeitung

  1. temperaturewas heated at 60° to 65°
  2. additionTo the aluminum chloride complex was added
  3. extractionextracted with ethyl acetate
  4. washThe extract was washed with water
  5. dry with materialdried over magnesium sulfate
  6. customevaporated in vacuo
  7. customThe residue was purified by column chromatography on silica gel (30 g) with a mixture of chloroform and methanol (50:1 to 10:1) as an eluent
  8. customThe eluates were evaporated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-55e9eda95ba84f9ab1a377be05d8c73c
Quelldatensatz
uspto-grants-1987_06
Patentnummer
US04675324

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