Ethyl Acetate → 6-Acetyl-4-(2-chlorophenyl)-9-methoxypyrrolo[3,4-c]carbazole-1,3(2H,6H)-dione

HRID 11159

Reaktionsgleichung

Reaktionsgleichung von HRID 11159
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[C:20]2[C:21](=[O:25])[NH:22][C:23](=[O:24])[C:19]=2[C:18]2[C:17]3[CH:16]=[C:15]([O:26][CH3:27])[CH:14]=[CH:13][C:12]=3[NH:11][C:10]=2[CH:9]=1.C(=O)(O)[O-].[K+].[C:33](OCC)(=[O:35])[CH3:34]>C(OC(=O)C)(=O)C.Cl(O)(=O)(=O)=O>[C:33]([N:11]1[C:10]2[CH:9]=[C:8]([C:3]3[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=3[Cl:1])[C:20]3[C:21](=[O:25])[NH:22][C:23](=[O:24])[C:19]=3[C:18]=2[C:17]2[CH:16]=[C:15]([O:26][CH3:27])[CH:14]=[CH:13][C:12]1=2)(=[O:35])[CH3:34]

Komponenten

6

Edukt 3

HCID 8857Ethyl AcetateHCID 516893Potassium BicarbonateHCID 118444834-(2-Chlorophenyl)-9-methoxypyrrolo[3,4-c]carbazole-1,3(2H,6H)-dione

Produkt 1

HCID 219804426-Acetyl-4-(2-chlorophenyl)-9-methoxypyrrolo[3,4-c]carbazole-1,3(2H,6H)-dioneAusbeute 80 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 24247Perchloric AcidKatalysatorHCID 7918Acetic AnhydrideLösungsmittel

Versuchsvorschrift

To a solution of carbazole (33) (45 mg, 0.12 mmol) prepared as described in example 79 in acetic anhydride (4.0 mL) was added 35% perchloric acid (2 drops). The resulting solution was stirred at room temperature for 30 minutes before being poured onto ice water, basified by the addition of solid potassium bicarbonate and extraction with ethyl acetate. The organic phase was dried, the drying agent was removed and the solution was concentrated to dryness. Chromatography on silica eluting with ethyl acetate/hexane (2:3), followed by trituration from ethyl acetate gave acetamide (338) (40 mg, 80%) as a pale yellow powder, mp 277–280° C. 1H NMR δ [(CD3)2SO] 11.46 (br s, 1H), 8.74 (d, J=2.8 Hz, 1H), 8.53 (s, 1H), 8.17 (d, J=9.2 Hz, 1H), 7.60 (m, 1H), 7.54–7.47 (m, 3H), 7.32 (dd, J=9.2, 2.8 Hz, 1H), 3.93 (s, 3H), 2.91 (s, 3H). Found: C, 65.50; H, 3.49; N, 6.61. C23H15ClN2O4.1/4H2O requires: C, 65.26; H, 3.69; N, 6.62.

Aufarbeitung

  1. additionbefore being poured onto ice water
  2. customThe organic phase was dried
  3. customthe drying agent was removed
  4. concentrationthe solution was concentrated to dryness

Quellen und Nachweise

ORD-Eintrag
ord-ff6f51d07f50479399583ee3c6d0baf6
Quelldatensatz
uspto-grants-2006_08
Patentnummer
US07094798B1

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