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

HRID 1742626노트

반응식

HRID 1742626 반응식
[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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-ee7a43e048b24321abba546a90b86080
출처 데이터셋
uspto-grants-1994_08
특허 번호
US05340819

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