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Sulfuric Acid → 3-Acetyl-4-(3,4-dimethoxyphenyl)-6,7-dimethoxy-2-methylquinoline

HRID 1684570
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1684570
S(=O)(=O)(O)O.[NH2:6][C:7]1[CH:24]=[C:23]([O:25][CH3:26])[C:22]([O:27][CH3:28])=[CH:21][C:8]=1[C:9]([C:11]1[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[C:13]([O:19][CH3:20])[CH:12]=1)=O.[C:29]([CH2:32][C:33](=O)[CH3:34])(=[O:31])[CH3:30]>C(O)(=O)C>[C:29]([C:32]1[C:33]([CH3:34])=[N:6][C:7]2[C:8]([C:9]=1[C:11]1[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[C:13]([O:19][CH3:20])[CH:12]=1)=[CH:21][C:22]([O:27][CH3:28])=[C:23]([O:25][CH3:26])[CH:24]=2)(=[O:31])[CH3:30]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 1118Sulfuric AcidHCID 31261AcetylacetoneHCID 99269672-Amino-4,5,3',4'-tetramethoxybenzophenone

Produkt 1

HCID 190398893-Acetyl-4-(3,4-dimethoxyphenyl)-6,7-dimethoxy-2-methylquinolineAusbeute 82 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 176Acetic AcidLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

Conc. sulfuric acid (0.185 ml ) was added to a mixture of 2-amino-4,5,3',4'-tetramethoxybenzophenone (10.0 g), acetylacetone (3.78 g) and acetic acid (75 ml), and the mixture was stirred at 100° C. for 2.5 hours. The reaction mixture was concentrated under reduced pressure. The residue was poured into water and made alkaline with 2N sodium hydroxide, and extracted with chloroform. The chloroform layer was washed with water and dried over magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was subjected to column chromatography on silica gel. The fractions eluted with chloroform-ethanol (20:1, v/v) gave 3-acetyl-4-(3,4-dimethoxyphenyl )-6,7-dimethoxy-2-methyl-quinoline (9.78 g, 82%). This compound was recrystallized from dichloromethane-ethanol to give colorless prisms, mp. 210°-211° C.

Aufarbeitung

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. additionThe residue was poured into water
  3. extractionextracted with chloroform
  4. washThe chloroform layer was washed with water
  5. dry with materialdried over magnesium sulfate
  6. customthe solvent was evaporated under reduced pressure
  7. washThe fractions eluted with chloroform-ethanol (20:1

Quellen und Nachweise

ORD-Eintrag
ord-fbcc5e3df8d6401fb0e024afd5a354a4
Quelldatensatz
uspto-grants-1997_06
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05641788

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