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

HRID 542513Notes

Reaction equation

HRID 542513 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.[CH3:13][C:14]1[NH:15][C:16]([N+:19]([O-:21])=[O:20])=[CH:17][N:18]=1.C(=O)([O-])[O-].[K+].[K+]>CN1CCCC1=O>[CH3:13][C:14]1[N:15]([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:16]([N+:19]([O-:21])=[O:20])=[CH:17][N:18]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 127602-Methyl-5-nitroimidazoleHCID 117758245-Bromo-1,6-naphthyridin-2(1H)-one

Product 1

HCID 103558105-(2-methyl-5-nitro-1H-imidazol-1-yl)-1,6-naphthyridin-2-(1H)-oneYield 66.7%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

A mixture containing 5.6 g of 5-bromo-1,6-naphthyridin-2(1H)-one, 12.7 g of 2-methyl-5-nitro-1H-imidazole, 3.45 g of anhydrous potassium carbonate and 50 ml of N-methylpyrrolidinone was refluxed for 5.5 hours, cooled and concentrated in vacuo to remove most of the solvent. To the concentrate was added 100 ml of water and 10 ml of 35% aqueous sodium hydroxide; and, the mixture was treated with decolorizing charcoal and filtered. The filtrate was acidified with acetic acid and the precipitate was collected, washed with water, dried, recrystallized from dimethylformamide, and dried in a vacuum oven at 90°-95° C. to yield 4.5 g of 5-(2-methyl-5-nitro-1H-imidazol-1-yl)-1,6-naphthyridin-2-(1H)-one, m.p. >300° C.

Workup

  1. temperaturewas refluxed for 5.5 hours
  2. temperaturecooled
  3. concentrationconcentrated in vacuo
  4. customto remove most of the solvent
  5. additionTo the concentrate was added 100 ml of water and 10 ml of 35% aqueous sodium hydroxide
  6. additionand, the mixture was treated with decolorizing charcoal
  7. filtrationfiltered
  8. customthe precipitate was collected
  9. washwashed with water
  10. customdried
  11. customrecrystallized from dimethylformamide
  12. customdried in a vacuum oven at 90°-95° C.

Sources & evidence

ORD record
ord-13c688ef2b4744d89847b6b5232526f1
Source dataset
uspto-grants-1987_04
Patent number
US04657915

Reaction notes

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