Methyl iodide → 5-Methoxyquinoxaline

HRID 2374156

Reaction equation

HRID 2374156 reaction equation
[N:1]1[C:10]2[CH:9]=[CH:8][CH:7]=[C:6]([OH:11])[C:5]=2[N:4]=[CH:3][CH:2]=1.[C:12]([O-])([O-])=O.[K+].[K+].IC>CN(C=O)C>[CH3:12][O:11][C:6]1[CH:7]=[CH:8][CH:9]=[C:10]2[C:5]=1[N:4]=[CH:3][CH:2]=[N:1]2

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 1356902745-Quinoxalinol

Product 1

HCID 132383925-Methoxyquinoxaline

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

To quinoxalin-5-ol (0.43 g) dissolved in DMF (6 ml) was added K2CO3 (2.5 eq.) and KI (0.2 eq.). To this mixture was then added dropwise iodomethane (1.2 eq.). The resulting mixture then heated to 50° C. overnight. The reaction mixture was subsequently partitioned between satd. NaHCO3 and EtOAc, the EtOAc layer backwashed with water and brine, dried over Na2SO4, and concentrated to dryness under vacuum. The crude material was then purified by SGC (MeOH:DCM) affording 5-methoxyquinoxaline. MS (ESI+) for m/z 160 [M+H]+.

Workup

  1. customThe reaction mixture was subsequently partitioned between satd
  2. dry with materialdried over Na2SO4
  3. concentrationconcentrated to dryness under vacuum
  4. customThe crude material was then purified by SGC (MeOH:DCM)

Sources & evidence

ORD record
ord-c80d808245104e7db92fadefdc7f9a71
Source dataset
uspto-grants-2008_12
Patent number
US07462600B2

Linked notes

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