Methyl-6-methoxy-2-indolecarboxylate → 6-methoxy-2-methyl-1H-indole

HRID 907119Notes

Reaction equation

HRID 907119 reaction equation
[H-].[H-].[H-].[H-].[Li+].[Al+3].[CH3:7][O:8][C:9]1[CH:17]=[C:16]2[C:12]([CH:13]=[C:14]([C:18](OC)=O)[NH:15]2)=[CH:11][CH:10]=1>O1CCOCC1>[CH3:7][O:8][C:9]1[CH:17]=[C:16]2[C:12]([CH:13]=[C:14]([CH3:18])[NH:15]2)=[CH:11][CH:10]=1

Participants

4

Reactant 2

HCID 688173Methyl-6-methoxy-2-indolecarboxylateHCID 21226445Aluminium lithium hydride

Product 1

HCID 108447096-methoxy-2-methyl-1H-indoleYield 61%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

To a suspension of LiAlH4 (7.6 g, 0.2 mol) in dioxane (100 mL) was added dropwise a solution of methyl 6-methoxy-1H-indole-2-carboxylate (8.2 g, 0.04 mol) in dioxane (50 mL) at 0° C. After the addition, the mixture was stirred at room temperature for 1 h and then heated at reflux for 5 h. After cooling to 0° C., the reaction was quenched by water (dropwise) and then 15% aqueous NaOH. After stirring at room temperature for 1 h, the mixture was filtered through Celite. The solid was washed with large amount of EtOAc. The solvent was washed with brine, dried over Na2SO4 and evaporated under vacuum. The residue was purified by flash column chromatography on silica gel using EtOAc/petroleum ether (1/5) as eluent to yield 61% of 6-methoxy-2-methyl-1H-indole.

Workup

  1. additionAfter the addition
  2. temperatureheated
  3. temperatureat reflux for 5 h
  4. temperatureAfter cooling to 0° C.
  5. customthe reaction was quenched by water (dropwise) and then 15% aqueous NaOH
  6. stirringAfter stirring at room temperature for 1 h
  7. filtrationthe mixture was filtered through Celite
  8. washThe solid was washed with large amount of EtOAc
  9. washThe solvent was washed with brine
  10. dry with materialdried over Na2SO4
  11. customevaporated under vacuum
  12. customThe residue was purified by flash column chromatography on silica gel

Sources & evidence

ORD record
ord-74ec7d9d56b144bdb7cbe0cc6e67e0c0
Source dataset
uspto-grants-2011_09
Patent number
US08013006B2

Reaction notes

Loading…