2-[2-nitro-4-(trifluoromethyl)phenyl]-1H-benz[de]isoquinoline-1,3(2H)-dione → 11-(trifluoromethyl)-7H-benzimidazo[2,1-a]benz[de]isoquinoline-7-one

HRID 652010

反応式

HRID 652010 の反応式
[N+:1]([C:4]1[CH:9]=[C:8]([C:10]([F:13])([F:12])[F:11])[CH:7]=[CH:6][C:5]=1[N:14]1[C:23](=[O:24])[C:22]2[CH:25]=[CH:26][CH:27]=[C:20]3[C:21]=2[C:16](=[CH:17][CH:18]=[CH:19]3)[C:15]1=O)([O-])=O.[H][H]>[Pd].C(O)(=O)C>[F:13][C:10]([F:12])([F:11])[C:8]1[CH:7]=[CH:6][C:5]2[N:14]3[C:23](=[O:24])[C:22]4=[CH:25][CH:26]=[CH:27][C:20]5[C:21]4=[C:16]([CH:17]=[CH:18][CH:19]=5)[C:15]3=[N:1][C:4]=2[CH:9]=1

参加物

5

反応物 2

HCID 201990122-[2-nitro-4-(trifluoromethyl)phenyl]-1H-benz[de]isoquinoline-1,3(2H)-dioneHCID 178418361HCID 178418361、化合物

生成物 1

HCID 1320618311-(trifluoromethyl)-7H-benzimidazo[2,1-a]benz[de]isoquinoline-7-one収率 59%

試薬・触媒・溶媒 2

HCID 23938Palladium触媒HCID 176Acetic Acid溶媒

実験手順

2-[2-nitro-4-(trifluoromethyl)phenyl]-1H-benz[de]isoquinoline-1,3(2H)-dione, 134.3 g. (0.347 m.), was hydrogenated at 55° C. in 600 ml. of glacial acetic acid with 15 g. of palladium-on-carbon (5 percent) at 60 psi. The temperature rose to about 100° C., and after 1.5 hours, three equivalents of hydrogen were absorbed with the temperature returning to room temperature. The reaction mixture was heated to boiling and filtered to remove the catalyst. Upon cooling, the precipitated product was collected and washed with 2B ethanol. Recrystallization from N,N-dimethylformamide yielded about 69.2 g. (59 percent yield) of 11-(trifluoromethyl)-7H-benzimidazo[2,1-a]benz[de]isoquinoline-7-one, m.p. about 212°-214° C.

後処理

  1. customwas hydrogenated at 55° C. in 600 ml
  2. customrose to about 100° C.
  3. customreturning to room temperature
  4. temperatureThe reaction mixture was heated
  5. filtrationfiltered
  6. customto remove the catalyst
  7. temperatureUpon cooling
  8. customthe precipitated product was collected
  9. washwashed with 2B ethanol
  10. customRecrystallization from N,N-dimethylformamide
  11. customyielded about 69.2 g

出典と根拠

ORDレコード
ord-314d90c2251c4eee80a006c35fff03aa
出典データセット
uspto-grants-1987_06
特許番号
US04670442

関連ノート

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