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 1648812

반응식

HRID 1648812 반응식
[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

참가 물질

5

반응물 2

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

생성물 1

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

시약·촉매·용매 2

HCID 23938Palladium촉매HCID 176Acetic Acid용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-978f1a0acc9a45df827a3e61d5bfc742
출처 데이터셋
uspto-grants-1983_11
특허 번호
US04413126

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