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

HRID 375104Notes

Reaction equation

HRID 375104 reaction equation
[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

Participants

5

Reactant 3

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

Product 1

HCID 199589339-(3-Trifluoromethylphenyl)-3,4,6,7,9,10-hexahydro-1,8(2H,5H)-acridinedioneYield 176.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-42131c688bd84a8590a8cf871ec39992
Source dataset
uspto-grants-1996_01
Patent number
US05484792

Reaction notes

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