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

HRID 2353925Notes

Reaction equation

HRID 2353925 reaction equation
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]

Participants

3

Reactant 2

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

Product 1

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

Conditions

Temperature
80 °C

Procedure

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 (DMSO-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).

Workup

  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

Sources & evidence

ORD record
ord-13b2e193704f4b339faf59bcec1d924b
Source dataset
uspto-grants-2010_07
Patent number
US07749992B2

Reaction notes

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