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

HRID 375104ノート

反応式

HRID 375104 の反応式
[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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-42131c688bd84a8590a8cf871ec39992
出典データセット
uspto-grants-1996_01
特許番号
US05484792

反応ノート

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