Ethanol → 2-(Hydroxymethyl)-6,7-dimethoxy-3-methyl-quinoxaline

HRID 614455Notes

Reaction equation

HRID 614455 reaction equation
Br[CH2:2][C:3]1[C:12]([CH3:13])=[N:11][C:10]2[C:5](=[CH:6][C:7]([O:16][CH3:17])=[C:8]([O:14][CH3:15])[CH:9]=2)[N:4]=1.C(=O)([O-])[O-:19].[Na+].[Na+].C(O)C>O>[OH:19][CH2:2][C:3]1[C:12]([CH3:13])=[N:11][C:10]2[C:5](=[CH:6][C:7]([O:16][CH3:17])=[C:8]([O:14][CH3:15])[CH:9]=2)[N:4]=1

Participants

5

Reactant 3

HCID 702EthanolHCID 10340Sodium CarbonateHCID 233493172-(Bromomethyl)-6,7-dimethoxy-3-methyl-quinoxaline

Product 1

HCID 205596382-(Hydroxymethyl)-6,7-dimethoxy-3-methyl-quinoxaline

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

8.9 g (30 mmols) of 2-(bromomethyl)-6,7-dimethoxy-3-methyl-quinoxaline are suspended in a mixture of 158 g (1.5 mols) of sodium carbonate, 350 ml of water and 100 ml of ethanol. The suspension is boiled under reflux for four hours. 300 ml of water are then added and the resulting mixture is extracted with three times 120 ml of chloroform. The organic phase is dried over magnesium sulphate. The solvent is evaporated in vacuo. The solid residue is recrystallised from methanol. This gives 3.5 g (50%) of a white powder.

Workup

  1. temperatureunder reflux for four hours
  2. extractionthe resulting mixture is extracted with three times 120 ml of chloroform
  3. dry with materialThe organic phase is dried over magnesium sulphate
  4. customThe solvent is evaporated in vacuo
  5. customThe solid residue is recrystallised from methanol

Sources & evidence

ORD record
ord-e71c7c9e780c4feb85e951d5eba8d659
Source dataset
uspto-grants-1979_03
Patent number
US04145217

Reaction notes

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