Water → Methyl 3-chloro-2-methoxy-7-methylquinoxaline-6-carboxylate

HRID 1807846Notes

Reaction equation

HRID 1807846 reaction equation
Cl[C:2]1[C:11]([Cl:12])=[N:10][C:9]2[C:4](=[CH:5][C:6]([CH3:17])=[C:7]([C:13]([O:15][CH3:16])=[O:14])[CH:8]=2)[N:3]=1.[CH3:18][O-:19].[Na+].C(Cl)(Cl)Cl.O>CO>[Cl:12][C:11]1[C:2]([O:19][CH3:18])=[N:3][C:4]2[C:9]([N:10]=1)=[CH:8][C:7]([C:13]([O:15][CH3:16])=[O:14])=[C:6]([CH3:17])[CH:5]=2

Participants

6

Reactant 4

HCID 962WaterHCID 6212ChloroformHCID 10942334Sodium MethoxideHCID 58575027Methyl 2,3-dichloro-7-methylquinoxaline-6-carboxylate

Product 1

HCID 58575046Methyl 3-chloro-2-methoxy-7-methylquinoxaline-6-carboxylate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent3×

Procedure

Under cooling in an ice-acetone bath, to a mixed liquid of 10.0 g of methyl 2,3-dichloro-7-methylquinoxaline-6-carboxylate in methanol was added dropwise a mixed liquid of 8.54 g of a 28% sodium methoxide solution in methanol and 80.0 mL of methanol over 6 hours. After stirring at the same temperature for 1 hour, the mixture was warmed to room temperature, followed by stirring for 1 hour. To the reaction mixture were added chloroform and water, followed by extraction with chloroform, and the organic layer was washed with saturated brine and then dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure to obtain 10.1 g of methyl 3-chloro-2-methoxy-7-methylquinoxaline-6-carboxylate as a pale yellow solid.

Workup

  1. stirringby stirring for 1 hour
  2. extractionfollowed by extraction with chloroform
  3. washthe organic layer was washed with saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customThe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-f0ce668db19f480b95597f8b6f1591dc
Source dataset
uspto-grants-2013_01
Patent number
US08357688B2

Reaction notes

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