Acetic Anhydride → 2,3-Dihydro-5-hydroxy-4,7-dimethyl-1H-indole-1-carbaldehyde

HRID 985578Notes

Reaction equation

HRID 985578 reaction equation
[C:1](OC(=O)C)(=[O:3])C.[CH3:8][C:9]1[C:17]([OH:18])=[CH:16][C:15]([CH3:19])=[C:14]2[C:10]=1[CH2:11][CH2:12][NH:13]2>C(O)=O>[OH:18][C:17]1[C:9]([CH3:8])=[C:10]2[C:14](=[C:15]([CH3:19])[CH:16]=1)[N:13]([CH:1]=[O:3])[CH2:12][CH2:11]2

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 225068232,3-Dihydro-4,7-dimethyl-1H-indol-5-ol

Product 1

HCID 225068342,3-Dihydro-5-hydroxy-4,7-dimethyl-1H-indole-1-carbaldehydeYield 37%

Reagents, catalysts & solvents 1

HCID 284Formic AcidSolvent

Procedure

Acetic anhydride (25 ml, 264 mmol) was added at room temperature to formic acid (75 ml) and stirred for 30 minutes. To the solution, 2,3-dihydro-4,7-dimethyl-1H-indol-5-ol (14.4 g, 88 mmol) was added and the mixture was stirred for 2 hours. The reaction mixture was concentrated under reduced pressure, and the residue was dissolved in a chloroform methanol solution and washed: with a saturated aqueous solution of sodium hydrogen carbonate. The organic layer was washed with saturated brine and dried over sodium sulfate, and then the solvent was removed under reduced pressure. The resultant residue was washed with diisopropyl ether to obtain 6.2 g of the title compound.

Workup

  1. stirringthe mixture was stirred for 2 hours
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. dissolutionthe residue was dissolved in a chloroform methanol solution
  4. washwashed
  5. washThe organic layer was washed with saturated brine
  6. dry with materialdried over sodium sulfate
  7. customthe solvent was removed under reduced pressure
  8. washThe resultant residue was washed with diisopropyl ether

Sources & evidence

ORD record
ord-2a85e356c7dd40b5b12ef041fd5f8ebc
Source dataset
uspto-grants-2005_03
Patent number
US06872718B1

Reaction notes

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