1,3-Cyclohexanedione → 9-(3-Trifluoromethylphenyl)-3,4,6,7,9,10-hexahydro-1,8(2H,5H)-acridinedione

HRID 1742626Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1742626
[F:1][C:2]([F:12])([F:11])[C:3]1[CH:4]=[C:5]([CH:8]=[CH:9][CH:10]=1)[CH:6]=O.[C:13]1(=[O:20])[CH2:18][CH2:17][CH2:16][C:15](=O)[CH2:14]1.[C:21]([O-:24])(=O)[CH3:22].[NH4+:25]>C(O)C>[F:1][C:2]([F:12])([F:11])[C:3]1[CH:4]=[C:5]([CH:6]2[C:14]3[C:13](=[O:20])[CH2:18][CH2:17][CH2:16][C:15]=3[NH:25][C:3]3[CH2:10][CH2:9][CH2:22][C:21](=[O:24])[C:2]2=3)[CH:8]=[CH:9][CH:10]=1

Komponenten

5

Edukt 3

HCID 104341,3-CyclohexanedioneHCID 679903-(Trifluoromethyl)benzaldehydeHCID 517165Ammonium Acetate

Produkt 1

HCID 199589339-(3-Trifluoromethylphenyl)-3,4,6,7,9,10-hexahydro-1,8(2H,5H)-acridinedioneAusbeute 176,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

A stirred mixture of 3-trifluoromethylbenzaldehyde (3.48 g), 1,3-cyclohexanedione (4.49 g), ammonium acetate (2.31 g) and ethanol (40 mL) was refluxed for 18 hours. The mixture was cooled and the yellow needles were collected, washed with water and dried in vacuo to give the title compound (6.38 g); mp >300 C; NMR: 1.7-2.0 (m,4), 2.19-2.25 (m,4), 2.50-2.56 (m,4), 4.98 (s,1), 7.41 (s,3), 7.48 (s,1), 9.48 (s,1); MS: m/z=362(M+1). Found for C20H18F3NO2 : C, 66.44; H, 5.00; N, 3.80.

Aufarbeitung

  1. temperaturewas refluxed for 18 hours
  2. temperatureThe mixture was cooled
  3. customthe yellow needles were collected
  4. washwashed with water
  5. customdried in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-ee7a43e048b24321abba546a90b86080
Quelldatensatz
uspto-grants-1994_08
Patentnummer
US05340819

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