Hydrochloric Acid → 5,7-Dimethylindole

HRID 268676Notes

Reaction equation

HRID 268676 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.Cl.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

5

Reactant 3

HCID 313Hydrochloric AcidHCID 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% HCl 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. stirringwas stirred 20 minutes
  2. extractionextracted with ethyl acetate
  3. dry with materialExtracts were dried over magnesium sulfate
  4. customevaporated to dryness

Sources & evidence

ORD record
ord-df40a1c683f744a0950f484c0ecc2580
Source dataset
uspto-grants-2008_11
Patent number
US07446122B2

Reaction notes

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