Methyl 5-chloro-1H-indole-2-carboxylate → HCID 22451271, compound

HRID 2185699Notes

Reaction equation

HRID 2185699 reaction equation
[Cl: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>[Cl: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 4777711Methyl 5-chloro-1H-indole-2-carboxylateHCID 5462224Magnesium

Product 1

HCID 22451271HCID 22451271, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Methyl 5-chloroindole-2-carboxylate (0.6 g, 2.87 mmol) and magnesium shavings (0.34 g, 14.3 mmol) were suspended in methanol (40 ml) and the mixture was stirred for 8 h. The mixture was filtered, treated with methylene chloride (100 ml) and washed with NH4Cl solution. The organic fraction was dried (Na2SO4) and the solvent removed in order to give a solid which was purified by chromatography on a column of silica gel, using a 7/3 petroleum/ethyl acetate mixture as eluent. The product was isolated in the form of a yellow solid.

Workup

  1. filtrationThe mixture was filtered
  2. additiontreated with methylene chloride (100 ml)
  3. washwashed with NH4Cl solution
  4. dry with materialThe organic fraction was dried (Na2SO4)
  5. customthe solvent removed in order
  6. customto give a solid which
  7. customwas purified by chromatography on a column of silica gel
  8. customThe product was isolated in the form of a yellow solid

Sources & evidence

ORD record
ord-936e5b66c1db428b8d8cb84221f199de
Source dataset
uspto-grants-2002_06
Patent number
US06403561B1

Reaction notes

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