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

HRID 375104Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 375104
[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-42131c688bd84a8590a8cf871ec39992
Quelldatensatz
uspto-grants-1996_01
Patentnummer
US05484792

Notizen zur Reaktion

Wird geladen…