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

HRID 11159

Reaction equation

HRID 11159 reaction equation
[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]

Participants

6

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 24247Perchloric AcidCatalystHCID 7918Acetic AnhydrideSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-ff6f51d07f50479399583ee3c6d0baf6
Source dataset
uspto-grants-2006_08
Patent number
US07094798B1

Linked notes

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