Dichloromethane → Methyl 4-methoxy-2,3-dihydro-1H-indole-2-carboxylate

HRID 2185678Notes

Reaction equation

HRID 2185678 reaction equation
[CH3:1][O:2][C:3]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:4]=1[CH:5]=[C:6]([C:12]([O:14][CH2:15]C)=[O:13])[NH:7]2.[Mg].ClCCl.[Cl-].[NH4+]>CO>[CH3:1][O:2][C:3]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:4]=1[CH2:5][CH:6]([C:12]([O:14][CH3:15])=[O:13])[NH:7]2

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 25517Ammonium ChlorideHCID 5462224MagnesiumHCID 11458647Ethyl 4-methoxy-1H-indole-2-carboxylate

Product 1

HCID 22451269Methyl 4-methoxy-2,3-dihydro-1H-indole-2-carboxylate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Ethyl 4-methoxyindole-2-carboxylate (0.95 g, 4.33 mmol) was dissolved in methanol (10 ml) and magnesium shavings (0.471 g, 19.37 mmol) were then added, with stirring, at room temperature under a nitrogen atmosphere. After the reaction started, a water bath was used to maintain the reaction temperature between 15-20° C. This mixture was stirred overnight. At the end of the reaction, dichloromethane (200 ml) was added to the mixture, followed by ammonium chloride solution (200 ml). The organic phase was separated out and the aqueous phase was extracted with dichloromethane (3×50 ml). The combined organic phases were dried over magnesium sulphate and the solvent was removed to give a brown oil.

Workup

  1. customa water bath was used
  2. temperatureto maintain the reaction temperature between 15-20° C
  3. stirringThis mixture was stirred overnight
  4. additionwas added to the mixture
  5. customThe organic phase was separated out
  6. extractionthe aqueous phase was extracted with dichloromethane (3×50 ml)
  7. dry with materialThe combined organic phases were dried over magnesium sulphate
  8. customthe solvent was removed
  9. customto give a brown oil

Sources & evidence

ORD record
ord-65b7b2ee7dfd4a14b98e1cc2a6764b50
Source dataset
uspto-grants-2002_06
Patent number
US06403561B1

Reaction notes

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