Aniline → 2-Hydroxy-N-phenyl-11H-benzo[a]carbazole-3-carboxamide

HRID 654349

Reaktionsgleichung

Reaktionsgleichung von HRID 654349
[OH:1][C:2]1[C:3]([C:19](OC2C=CC=CC=2)=[O:20])=[CH:4][C:5]2[C:6]([CH:18]=1)=[C:7]1[C:15](=[CH:16][CH:17]=2)C2C(=CC=CC=2)[NH:8]1.[NH2:28][C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1>CN1C(=O)CCC1>[OH:1][C:2]1[C:3]([C:19]([NH:28][C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)=[O:20])=[CH:4][C:5]2[C:6]([CH:18]=1)=[C:7]1[C:15](=[CH:16][CH:17]=2)[C:3]2[C:2](=[CH:18][CH:6]=[CH:5][CH:4]=2)[NH:8]1

Komponenten

4

Edukt 2

HCID 6115AnilineHCID 19933809Phenyl2-hydroxy-11H-benzo[a]carbazole-3-carboxylate

Produkt 1

HCID 155969922-Hydroxy-N-phenyl-11H-benzo[a]carbazole-3-carboxamideAusbeute 178,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 13387N-methyl-2-pyrrolidoneLösungsmittel

Versuchsvorschrift

The phenyl 2-hydroxy-11H-benzo(a)carbazole-3-carboxylate obtained from Example I (5 grams, 14 millimoles), aniline (27.5 grams, 280 millimoles) and 15 milliliters of N-methyl pyrrolidinone were charged in a 100 milliliter 3-neck flask equipped with a magnetic stirrer and a nitrogen inlet. The resulting mixture was stirred and was heated to reflux at an oil bath temperature of ~250° C. under a nitrogen atmosphere. After 3 hours, TLC analysis revealed that all the starting phenyl ester was consumed. The mixture was cooled to room temperature and was poured into a 1 liter beaker containing 400 milliliters of ice cold 5 percent HCl. The yellow precipitate obtained was isolated by filtration. After washing with water (~200 milliliters) and ~20 milliliters of methanol and vacuum drying, 5.0 grams of crude product resulted. This product was then recrystallized from a mixture of DMF/MeOH/H2O (~30 milliliter each) yielding 4.4 grams (88 percent) of 2-hydroxy-11 H-benzo(a)carbazole-3-carboxanilide.

Aufarbeitung

  1. customequipped with a magnetic stirrer and a nitrogen inlet
  2. temperaturewas heated
  3. temperatureto reflux at an oil bath temperature of ~250° C. under a nitrogen atmosphere
  4. customwas consumed
  5. additionwas poured into a 1 liter beaker
  6. additioncontaining 400 milliliters of ice cold 5 percent HCl
  7. customThe yellow precipitate obtained
  8. customwas isolated by filtration
  9. washAfter washing with water (~200 milliliters) and ~20 milliliters of methanol and vacuum
  10. customdrying
  11. custom5.0 grams of crude product resulted
  12. customThis product was then recrystallized from a mixture of DMF/MeOH/H2O (~30 milliliter each)

Quellen und Nachweise

ORD-Eintrag
ord-6e072f5d953642aa8729286d4dc77b6a
Quelldatensatz
uspto-grants-1992_07
Patentnummer
US05130443

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