Sulfuric Acid → Cyclopent[f]indole-2,3-dione, 1,5,6,7-tetrahydro-

HRID 507073

반응식

HRID 507073 반응식
ON=[CH:3][C:4]([NH:6][C:7]1[CH:8]=[C:9]2[C:13](=[CH:14][CH:15]=1)[CH2:12][CH2:11][CH2:10]2)=[O:5].S(=O)(=O)(O)[OH:17]>>[NH:6]1[C:7]2[C:15](=[CH:14][C:13]3[CH2:12][CH2:11][CH2:10][C:9]=3[CH:8]=2)[C:3](=[O:17])[C:4]1=[O:5]

참가 물질

3

반응물 2

HCID 1118Sulfuric AcidHCID 722820052-Hydroxyimino-N-indan-5-yl-acetamide

생성물 1

HCID 22560824Cyclopent[f]indole-2,3-dione, 1,5,6,7-tetrahydro-수율 77%

반응 조건

온도
80 °C

실험 절차

Add 2-hydroxyimino-N-indan-5-yl-acetamide (4.66 g, 22.84 mmol) in small portions at 65° C. to concentrated sulfuric acid (22 mL) and heat the mixture at 80° C. for 15 minutes. Cool to room temperature, pour into ice water (200 mL) and filter the precipitate. Dissolve the solid in warmed ethanol and leave to cool overnight. Filter the precipitate and wash with ethyl ether. Dry the solid to yield the title compound (3.3 g, 77%). 1H NMR (dimethyl sulfoxide-d6, 300 MHz) δ 1.98 (quintuplet, J=7.7 Hz, 2H), 2.76 (t, J=7.7 Hz, 2H), 2.85 (t, J=7.7 Hz, 2H), 6.74 (s, 1H), 7.28 (s, 1H). MS (ES−): 186 (M−H).

후처리

  1. temperatureCool to room temperature
  2. filtrationfilter the precipitate
  3. dissolutionDissolve the solid in warmed ethanol
  4. customleave
  5. temperatureto cool overnight
  6. filtrationFilter the precipitate
  7. washwash with ethyl ether
  8. customDry the solid

출처 및 근거

ORD 기록
ord-0b5f2ce785d6412ca4a0ab37ed05dafd
출처 데이터셋
uspto-grants-2010_08
특허 번호
US07786108B2

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