Potassium Carbonate → 5-(4,5-dimethyl-1H-imidazol-1-yl)-1,6-naphthyridin-2(1H)-one

HRID 542517Notes

Reaction equation

HRID 542517 reaction equation
Br[C:2]1[N:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][C:6](=[O:12])[NH:7]2.C(=O)([O-])[O-].[K+].[K+].[CH3:19][C:20]1[N:21]=[CH:22][NH:23][C:24]=1[CH3:25]>CN(C)C=O>[CH3:19][C:20]1[N:21]=[CH:22][N:23]([C:2]2[N:11]=[CH:10][CH:9]=[C:8]3[C:3]=2[CH:4]=[CH:5][C:6](=[O:12])[NH:7]3)[C:24]=1[CH3:25]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 753064,5-Dimethyl-1H-imidazoleHCID 117758245-Bromo-1,6-naphthyridin-2(1H)-one

Product 1

HCID 101056965-(4,5-dimethyl-1H-imidazol-1-yl)-1,6-naphthyridin-2(1H)-oneYield 48%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture containing 12.5 g of 5-bromo-1,6-naphthyridin-2(1H)-one, 300 ml of dimethylformamide, 13.8 g of anhydrous potassium carbonate, 10.8 g of 4,5-dimethylimidazole and 200 mg of cuprous bromide was refluxed with stirring for eight hours About 20 ml of the solvent was distilled off using a water separator to remove any moisture from the reaction mixture. The remaining reaction mixture was concentrated on a rotary evaporator. The residue was dissolved in water, acidified with acetic acid and evaporated to dryness on a rotary evaporator. The residue was treated with 50 ml of water and the brown solid was collected, washed with water, recrystallized from ethanol in the presence of decolorizing charcoal. The resulting pale yellow solid was dried at 80°-85° C. to yield 6.4 g of 5-(4,5-dimethyl-1H-imidazol-1-yl)-1,6-naphthyridin-2(1H)-one, m.p. 256°-258° C.

Workup

  1. temperaturewas refluxed
  2. distillationwas distilled off
  3. customto remove any moisture from the reaction mixture
  4. customThe remaining reaction mixture
  5. concentrationwas concentrated on a rotary evaporator
  6. dissolutionThe residue was dissolved in water
  7. customevaporated to dryness on a rotary evaporator
  8. additionThe residue was treated with 50 ml of water
  9. customthe brown solid was collected
  10. washwashed with water
  11. customrecrystallized from ethanol in the presence of decolorizing charcoal
  12. customThe resulting pale yellow solid was dried at 80°-85° C.

Sources & evidence

ORD record
ord-f29556efb5114a53aa2230b52b7194b0
Source dataset
uspto-grants-1987_04
Patent number
US04657915

Reaction notes

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