Potassium Carbonate → HCID 20368821, compound

HRID 616704Notes

Reaction equation

HRID 616704 reaction equation
[NH2:1][C:2]1[CH:11]=[C:10]([O:12][CH3:13])[C:9]2[C:4](=[CH:5][C:6]([O:16][CH3:17])=[C:7]([O:14][CH3:15])[CH:8]=2)[N:3]=1.C(=O)([O-])[O-].[K+].[K+].Br[CH2:25][C:26](=O)[C:27]([O:29][CH2:30][CH3:31])=[O:28]>CN(C)C=O>[CH3:13][O:12][C:10]1[C:9]2[C:4](=[CH:5][C:6]([O:16][CH3:17])=[C:7]([O:14][CH3:15])[CH:8]=2)[N:3]2[CH:25]=[C:26]([C:27]([O:29][CH2:30][CH3:31])=[O:28])[N:1]=[C:2]2[CH:11]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 66144Ethyl bromopyruvateHCID 203688284,6,7-Trimethoxyquinolin-2-amine

Product 1

HCID 20368821HCID 20368821, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To 50 ml. of N,N-dimethylformamide was added 5.2 g. (0.022 mole) of 2-amino-4,6,7-trimethoxyquinoline, and 3.38 g. (0.0244 mole) potassium carbonate. To the resulting slurry was added dropwise over 15 minutes 4.76 g. (0.0244 mole) ethyl bromopyruvate. The reaction mixture was stirred at room temperature 1.75 hours, during which the mixture became orange and a solid precipitated. Upon pouring onto 400 ml. of cold water a solid material formed which was filtered, dried, then dissolved in the minimum amount of chloroform. The solution was charged onto a column made up of 100 g. of silica gel in chloroform and elution with chloroform started. After 200 ml. of eluate was collected, elution with chloroform/ethanol (98:2 v/v) was started and 200 ml. fractions were collected. Fractions 1 through 4 were combined and evaporated to dryness to afford 3.0 g. of product. Recrystallization from benzene/cyclohexane yielded 2.7 g. of colorless solid, M.P. 195°-197° C.

Workup

  1. additionTo the resulting slurry was added dropwise over 15 minutes 4.76 g
  2. customa solid precipitated
  3. additionUpon pouring onto 400 ml
  4. customof cold water a solid material formed which
  5. filtrationwas filtered
  6. customdried
  7. dissolutiondissolved in the minimum amount of chloroform
  8. additionThe solution was charged onto a column
  9. washof silica gel in chloroform and elution with chloroform
  10. customof eluate was collected
  11. washelution with chloroform/ethanol (98:2 v/v)
  12. customfractions were collected
  13. customevaporated to dryness
  14. customto afford 3.0 g
  15. customRecrystallization from benzene/cyclohexane
  16. customyielded 2.7 g

Sources & evidence

ORD record
ord-abdac326e10a4c9cbdd14b0bdf604d28
Source dataset
uspto-grants-1978_02
Patent number
US04075343

Reaction notes

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