1H-Indole-2,3-dione, 5,7-dimethyl- (9CI) → 5,7-Dimethylindole

HRID 2249554Notes

Reaction equation

HRID 2249554 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]2[C:8](=[C:9]([CH3:11])[CH:10]=1)[NH:7][C:6](=O)[C:5]2=O.C(=O)(O)[O-].[Na+]>O1CCCC1>[CH3:1][C:2]1[CH:3]=[C:4]2[C:8](=[C:9]([CH3:11])[CH:10]=1)[NH:7][CH:6]=[CH:5]2

Participants

4

Reactant 2

HCID 382961H-Indole-2,3-dione, 5,7-dimethyl- (9CI)HCID 516892Sodium Bicarbonate

Product 1

HCID 5893955,7-Dimethylindole

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To solution of 5,7-dimethyl-1H-indole-2,3-dione in tetrahydrofuran at 0° C. was added 1.0 M solution of borane-tetrahydrofuran complex in tetrahydrofuran (40 mL). After stirred at room temperature overnight, a 5% HCI solution was added to the mixture and it was stirred 20 minutes. It was neutralized with saturated sodium bicarbonate solution and extracted with ethyl acetate. Extracts were dried over magnesium sulfate and evaporated to dryness to afford the title compound as oil.

Workup

  1. additiona 5% HCI solution was added to the mixture and it
  2. stirringwas stirred 20 minutes
  3. extractionextracted with ethyl acetate
  4. dry with materialExtracts were dried over magnesium sulfate
  5. customevaporated to dryness

Sources & evidence

ORD record
ord-6ad3c56d487d4689bdb745cfa4abed8c
Source dataset
uspto-grants-2008_01
Patent number
US07314886B2

Reaction notes

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