Methanol → HCID 54118280, compound

HRID 361627Notes

Reaction equation

HRID 361627 reaction equation
[CH3:1][C:2]1[CH:10]=[CH:9][C:8]([CH3:11])=[C:7]2[C:3]=1[CH:4]=[C:5]([C:12]([O:14][CH3:15])=[O:13])[NH:6]2.[Mg].CO>O>[CH3:1][C:2]1[CH:10]=[CH:9][C:8]([CH3:11])=[C:7]2[C:3]=1[CH2:4][CH:5]([C:12]([O:14][CH3:15])=[O:13])[NH:6]2

Participants

5

Reactant 3

HCID 887MethanolHCID 4714976methyl 4,7-dimethyl-1H-indole-2-carboxylateHCID 5462224Magnesium

Product 1

HCID 54118280HCID 54118280, compoundYield 79%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
0 °C

Procedure

A flask dried with heating was charged with 1.6 g (7.9 mmol) of methyl 4,7-dimethylindole-2-carboxylate and 3.8 g (158 mmol) of chipped magnesium. After addition of 400 ml of anhydrous methanol, the reaction mixture was stirred vigorously for 30 minutes. The flask was placed in an ice bath to cool the reaction mixture to 0° C., and the reaction mixture was stirred overnight. The reaction mixture was diluted with 300 ml of water, filtered and extracted with 100 ml of methylene chloride three times. The methylene chloride layers were combined, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The solids thus obtained were purified by silica gel column chromatography to provide 1.28 g of light red crystals. Yield: 79%

Workup

  1. customA flask dried
  2. temperaturewith heating
  3. customThe flask was placed in an ice bath
  4. stirringthe reaction mixture was stirred overnight
  5. filtrationfiltered
  6. extractionextracted with 100 ml of methylene chloride three times
  7. dry with materialdried over anhydrous magnesium sulfate
  8. concentrationconcentrated under reduced pressure
  9. customThe solids thus obtained
  10. customwere purified by silica gel column chromatography

Sources & evidence

ORD record
ord-e48df701c8a041c2ba914b4da5ce0e71
Source dataset
uspto-grants-1999_02
Patent number
US05866594

Reaction notes

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