Hydrochloric Acid → HCID 21491283, compound

HRID 1973366Notes

Reaction equation

HRID 1973366 reaction equation
Cl[C:2]1[C:3]([C:16]([O:18]CC)=[O:17])=[N:4][C:5]2[C:10]([N:11]=1)=[CH:9][C:8]([O:12][CH3:13])=[C:7]([O:14][CH3:15])[CH:6]=2.[CH3:21][O-:22].[Na+].Cl>O>[CH3:21][O:22][C:2]1[C:3]([C:16]([OH:18])=[O:17])=[N:4][C:5]2[C:10]([N:11]=1)=[CH:9][C:8]([O:12][CH3:13])=[C:7]([O:14][CH3:15])[CH:6]=2

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 10942334Sodium MethoxideHCID 12283441HCID 12283441, compound

Product 1

HCID 21491283HCID 21491283, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

3-Chloro-6,7-dimethoxy-2-quinoxalinecarboxylic acid, ethyl ester (3.5 g) was added to sodium methoxide (prepared from sodium (0.7 g) in methanol (250 ml)). The solution was heated under reflux for 2 hours. Water (50 ml) was added and the solution was heated under reflux for 45 minutes and cooled. 2N Hydrochloric acid was added to give a mixture of pH1 and the methanol was distilled off. Water (500 ml) was added and the solution was extracted with ethyl acetate. The extract was dried over magnesium sulphate, filtered and evaporated and the residue was crystallised from a mixture of ethyl acetate and light petroleum (b.p. 60°-80°). The product had m.p. 163°-164° (d) (54%).

Workup

  1. temperatureThe solution was heated
  2. temperatureunder reflux for 2 hours
  3. temperaturethe solution was heated
  4. temperatureunder reflux for 45 minutes
  5. temperaturecooled
  6. customto give
  7. additiona mixture of pH1
  8. distillationthe methanol was distilled off
  9. additionWater (500 ml) was added
  10. extractionthe solution was extracted with ethyl acetate
  11. dry with materialThe extract was dried over magnesium sulphate
  12. filtrationfiltered
  13. customevaporated
  14. customthe residue was crystallised from a mixture of ethyl acetate and light petroleum (b.p. 60°-80°)

Sources & evidence

ORD record
ord-615fc1e52ab34f3a8d1fba0b78bb37df
Source dataset
uspto-grants-1976_12
Patent number
US03997535

Reaction notes

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