Dimethylformamide → 5-(4-bromo-1H-imidazol-1-yl)-1,6-naphthyridin-2(1H)-one

HRID 542520Notes

Reaction equation

HRID 542520 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.[Br:13][C:14]1[N:15]=[CH:16][NH:17][CH:18]=1.CN(C)C=CC1NC(=O)C=CC=1C#N.CN(C)C=O>O.[OH-].[Na+].CN1CCCC1=O>[Br:13][C:14]1[N:15]=[CH:16][N:17]([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)[CH:18]=1

Participants

8

Reactant 4

HCID 6228DimethylformamideHCID 117758245-Bromo-1,6-naphthyridin-2(1H)-one2×HCID 544759082-[2-(Dimethylamino)ethenyl]-1,6-dihydro-6-oxo-3-pyridinecarbonitrileHCID 178418934HCID 178418934, compound

Product 1

HCID 100856475-(4-bromo-1H-imidazol-1-yl)-1,6-naphthyridin-2(1H)-oneYield 70.8%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 13387N-methyl-2-pyrrolidoneSolventHCID 14798Sodium HydroxideSolvent

Procedure

A stirred mixture containing 11.25 g of 5-bromo-1,6-naphthyridin-2(1H)-one, 16.6 g of 4-bromo-1H-imidazole and 100 ml of N-methylpyrrolidinone was heated in an oil bath at 135°-140° C. for 22 hours. The reaction mixture was cooled and diluted with 200 ml of water. The resulting precipitate was collected, washed with water, air-dried, combined with 1.5 g of 5-(4-bromo-1H-imidazol-1-yl)-1,6-naphthyridin-2(1H)-one prepared in another run starting with 1 58 g of 5-bromo-1,6-naphthyridin-2(1H)-one, recrystallized twice from dimethylformamide and dried in an Abderhalden drying pistol at 90° for 22 hours, after which the sample still contained 0.2 mol of dimethylformamide per mol of product. The material was then dissolved in 100 ml of 5% aqueous sodium hydroxide solution, the solution filtered and the filtrate solidified with acetic acid. The cottony solid that crystallized out was collected, washed with distilled water and dried in an oven at 100° C. over the weekend to produce 10.3 g of 5-(4-bromo-1H-imidazol-1-yl)- 1,6-naphthyridin-2(1H)-one, m.p. 278°-280° C.

Workup

  1. temperaturewas heated in an oil bath at 135°-140° C. for 22 hours
  2. temperatureThe reaction mixture was cooled
  3. customThe resulting precipitate was collected
  4. washwashed with water
  5. customair-dried
  6. customprepared in another run
  7. customrecrystallized twice from dimethylformamide
  8. customdried in an Abderhalden
  9. customdrying pistol at 90° for 22 hours
  10. filtrationthe solution filtered
  11. customThe cottony solid that crystallized out
  12. customwas collected
  13. washwashed with distilled water
  14. customdried in an oven at 100° C. over the weekend

Sources & evidence

ORD record
ord-22ecba14c24a4869929a736946dc16af
Source dataset
uspto-grants-1987_04
Patent number
US04657915

Reaction notes

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