4-Nitrophthalic acid anhydride → 9,9-Bis{4-(4-nitrophthalimido)phenyl}fluorene

HRID 129953Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 129953
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([C:21]3[CH:26]=[CH:25][C:24]([NH2:27])=[CH:23][CH:22]=3)[C:20]3[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=3[C:14]3[C:9]2=[CH:10][CH:11]=[CH:12][CH:13]=3)=[CH:4][CH:3]=1.[N+:28]([C:31]1[CH:32]=[C:33]2[C:38](=[O:39])O[C:35](=[O:36])[C:34]2=[CH:40][CH:41]=1)([O-:30])=[O:29]>C(O)(=O)C>[N+:28]([C:31]1[CH:32]=[C:33]2[C:38](=[O:39])[N:1]([C:2]3[CH:3]=[CH:4][C:5]([C:8]4([C:21]5[CH:22]=[CH:23][C:24]([N:27]6[C:38](=[O:39])[C:33]7=[CH:32][C:31]([N+:28]([O-:30])=[O:29])=[CH:41][CH:40]=[C:34]7[C:35]6=[O:36])=[CH:25][CH:26]=5)[C:9]5[CH:10]=[CH:11][CH:12]=[CH:13][C:14]=5[C:15]5[C:20]4=[CH:19][CH:18]=[CH:17][CH:16]=5)=[CH:6][CH:7]=3)[C:35](=[O:36])[C:34]2=[CH:40][CH:41]=1)([O-:30])=[O:29]

Komponenten

4

Edukt 2

HCID 2309764-Nitrophthalic acid anhydrideHCID 6315524,4'-(9-Fluorenylidene)dianiline

Produkt 1

HCID 30950489,9-Bis{4-(4-nitrophthalimido)phenyl}fluoreneAusbeute 73 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 176Acetic AcidLösungsmittel

Versuchsvorschrift

A mixture of 9,9-bis(4-aminophenyl)fluorene (3.5 g, 10 mmol) and 40 ml of acetic acid was stirred and then 4-nitrophthalic anhydride (4.1 g, 21 mmol) was added to the mixture. The resulting mixture was stirred and heated under reflux for 7 hours. After cooling, the beige-colored precipitate was filtered, washed with acetic acid (2×100 ml) and then with water (500 ml). The washed precipitate was recrystallized from dimethylformamide-methanol to provide the title compound as an off-white powder (5.1 g, 73% yield) having a melting point of 360°-363° C.

Aufarbeitung

  1. stirringThe resulting mixture was stirred
  2. temperatureheated
  3. temperatureunder reflux for 7 hours
  4. temperatureAfter cooling
  5. filtrationthe beige-colored precipitate was filtered
  6. washwashed with acetic acid (2×100 ml)
  7. customThe washed precipitate was recrystallized from dimethylformamide-methanol

Quellen und Nachweise

ORD-Eintrag
ord-97c7f8d9b1214636ab4d3c3c78378613
Quelldatensatz
uspto-grants-1995_11
Patentnummer
US05470987

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