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

Reaktionsgleichung

Reaktionsgleichung von HRID 652010
[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

Komponenten

5

Edukt 2

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 176Acetic AcidLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-314d90c2251c4eee80a006c35fff03aa
Quelldatensatz
uspto-grants-1987_06
Patentnummer
US04670442

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