Dichloromethane → HCID 13600823, compound

HRID 2185685Notes

Reaction equation

HRID 2185685 reaction equation
[CH3:1][C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[NH:4][C:3]=1[C:11]([O:13][CH2:14]C)=[O:12].[Mg].ClCCl.[NH4+].[Cl-]>CO>[CH3:1][CH:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[NH:4][CH:3]1[C:11]([O:13][CH3:14])=[O:12]

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 25517Ammonium ChlorideHCID 593963Ethyl 3-methyl-1H-indole-2-carboxylateHCID 5462224Magnesium

Product 1

HCID 13600823HCID 13600823, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Ethyl 3-methylindole-2-carboxylate (4.06 g, 20 mmol) was dissolved in methanol (50 ml) and magnesium shavings (2.431 g, 100 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. After the end of the reaction, dichloromethane (200 ml) was added to the mixture, followed by NH4Cl 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. additionwas added to the mixture
  4. customThe organic phase was separated out
  5. extractionthe aqueous phase was extracted with dichloromethane (3×50 ml)
  6. dry with materialThe combined organic phases were dried over magnesium sulphate
  7. customthe solvent was removed
  8. customto give a brown oil

Sources & evidence

ORD record
ord-78594162009b441f8a1e2c6ab0edfa76
Source dataset
uspto-grants-2002_06
Patent number
US06403561B1

Reaction notes

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