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

HRID 507073

反応式

HRID 507073 の反応式
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]

参加物

3

反応物 2

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

生成物 1

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

反応条件

温度
80 °C

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-0b5f2ce785d6412ca4a0ab37ed05dafd
出典データセット
uspto-grants-2010_08
特許番号
US07786108B2

関連ノート

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