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

HRID 11159

반응식

HRID 11159 반응식
[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]

참가 물질

6

반응물 3

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

생성물 1

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

시약·촉매·용매 2

HCID 24247Perchloric Acid촉매HCID 7918Acetic Anhydride용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-ff6f51d07f50479399583ee3c6d0baf6
출처 데이터셋
uspto-grants-2006_08
특허 번호
US07094798B1

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