Methyl 5-methyl-1H-indole-2-carboxylate → 185212-39-9

HRID 2185696Notes

Reaction equation

HRID 2185696 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6]([C:11]([O:13][CH3:14])=[O:12])=[CH:5]2.[Mg]>CO>[CH3:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][CH:6]([C:11]([O:13][CH3:14])=[O:12])[CH2:5]2

Participants

4

Reactant 2

HCID 4777680Methyl 5-methyl-1H-indole-2-carboxylateHCID 5462224Magnesium

Product 1

HCID 22451281185212-39-9

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
15 °C

Procedure

Methyl 5-methylindole-2-carboxylate (0.95 g, 5 mmol) and magnesium shavings (0.62 g, 25 mmol) were suspended in methanol (25 ml) and the mixture was stirred at 15° C. for 2 h. The mixture was filtered, diluted with methylene chloride (100 ml) and washed with NH4Cl solution. The organic phase was dried (Na2SO4) and the solvent removed to give the crude product, which was purified by chromatography on a column of silica gel, using a 7/3 petroleum/ethyl acetate mixture as eluent.

Workup

  1. filtrationThe mixture was filtered
  2. additiondiluted with methylene chloride (100 ml)
  3. washwashed with NH4Cl solution
  4. dry with materialThe organic phase was dried (Na2SO4)
  5. customthe solvent removed

Sources & evidence

ORD record
ord-ca96977d97b4463abe449ddbadbf5677
Source dataset
uspto-grants-2002_06
Patent number
US06403561B1

Reaction notes

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