Methanesulfonic Acid → 1,6,7,8-Tetrahydrocyclopenta[g]indole-2,3-dione

HRID 2353933Notes

Reaction equation

HRID 2353933 reaction equation
ON=[CH:3][C:4]([NH:6][C:7]1[CH:15]=[CH:14][CH:13]=[C:12]2[C:8]=1[CH2:9][CH2:10][CH2:11]2)=[O:5].CS(O)(=O)=[O:18]>>[NH:6]1[C:7]2[C:15](=[CH:14][CH:13]=[C:12]3[C:8]=2[CH2:9][CH2:10][CH2:11]3)[C:3](=[O:18])[C:4]1=[O:5]

Participants

3

Reactant 2

HCID 6395Methanesulfonic AcidHCID 727406282-Hydroxyimino-N-indan-4-yl-acetamide

Product 1

HCID 148855691,6,7,8-Tetrahydrocyclopenta[g]indole-2,3-dioneYield 72%

Procedure

Add 2-Hydroxyimino-N-indan-4-yl-acetamide (5.54 g, 27.1 mmol) in small portions at 80° C. to methanesulfonic acid (21 mL). Stir the mixture at this temperature for 25 min. Cool to room temperature, pour into ice water and filter the precipitate. Dissolve the solid in warmed 1N NaOH, and neutralize with acetic acid. Filter the resulting solid and acidify the filtrate with concentrated HCl. Filter the precipitate and wash with water. Dry the solid to yield the title compound (3.80 g, 72%). MS (ES−): 186 (M−H).

Workup

  1. filtrationfilter the precipitate
  2. dissolutionDissolve the solid in warmed 1N NaOH
  3. filtrationFilter the resulting solid
  4. filtrationFilter the precipitate
  5. washwash with water
  6. customDry the solid

Sources & evidence

ORD record
ord-f7450739ad024eed8ed6fa5aecc027db
Source dataset
uspto-grants-2010_07
Patent number
US07749992B2

Reaction notes

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