Methyl iodide → 2-Methoxy-5,6,7,8-tetrahydroquinoline

HRID 33770Notes

Reaction equation

HRID 33770 reaction equation
[NH:1]1[C:10]2[CH2:9][CH2:8][CH2:7][CH2:6][C:5]=2[CH:4]=[CH:3][C:2]1=[O:11].[CH3:12]I>C(Cl)(Cl)Cl>[CH3:12][O:11][C:2]1[CH:3]=[CH:4][C:5]2[CH2:6][CH2:7][CH2:8][CH2:9][C:10]=2[N:1]=1

Participants

4

Reactant 2

HCID 6328Methyl iodideHCID 2641061,2,5,6,7,8-Hexahydroquinolin-2-one

Product 1

HCID 181802832-Methoxy-5,6,7,8-tetrahydroquinoline

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a 0.33 M solution of 5,6,7,8-tetrahydroquinolin-2 (1H)-one in dry CHCl3 at room temperature was added 1.2 equiv of Ag2CO3 and 6 equiv of MeI. The final suspension was refluxed in the dark for 5 h. After allowing the reaction to cool to room temperature, the suspension was filtered through Celite and concentrated. The crude material was further purified by flash chromatography, eluting with a gradient from 100% hexanes to 10% EtOAc/hexanes to provide the title compound as a colorless oil.

Workup

  1. customthe reaction
  2. filtrationthe suspension was filtered through Celite
  3. concentrationconcentrated
  4. customThe crude material was further purified by flash chromatography
  5. washeluting with a gradient from 100% hexanes to 10% EtOAc/hexanes

Sources & evidence

ORD record
ord-b200f1e5c14d43cf9fb70cf511114e62
Source dataset
uspto-grants-2008_09
Patent number
US07429666B2

Reaction notes

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