Hydrogen Bromide → 6,8-Dibromo-1,7-naphthyridine

HRID 1006922Notes

Reaction equation

HRID 1006922 reaction equation
N[C:2]1[CH:3]=[C:4]2[C:9](=[C:10]([Br:12])[N:11]=1)[N:8]=[CH:7][CH:6]=[CH:5]2.[BrH:13].N([O-])=O.[Na+].[OH-].[Na+]>>[Br:13][C:2]1[CH:3]=[C:4]2[C:9](=[C:10]([Br:12])[N:11]=1)[N:8]=[CH:7][CH:6]=[CH:5]2

Participants

5

Reactant 4

HCID 260Hydrogen BromideHCID 14798Sodium HydroxideHCID 107043358-Bromo-1,7-naphthyridin-6-amineHCID 23668193Sodium Nitrite

Product 1

HCID 225032286,8-Dibromo-1,7-naphthyridineYield 34%

Procedure

To 6-amino-8-bromo-1,7-naphthyridine (6.554 g) synthesized according to Tetrahedron Letters, 12, 1233, 1966 was added 48% hydrobromic acid (55 ml). Sodium nitrite (4.141 g) was added thereto in small portions under ice-cooling, and the mixture was stirred overnight. The reaction mixture was basified by adding 5N sodium hydroxide thereto, and it was extracted with ethyl acetate. The resulting organic layer was washed with water, dried (over MgSO4) and evaporated. The resulting residue was purified by silica gel column chromatography (ethyl acetate/hexane system), to give the title compound as a yellowish orange solid (2.856 g, yield; 34%).

Workup

  1. temperaturein small portions under ice-cooling
  2. extractionit was extracted with ethyl acetate
  3. washThe resulting organic layer was washed with water
  4. dry with materialdried (over MgSO4)
  5. customevaporated
  6. customThe resulting residue was purified by silica gel column chromatography (ethyl acetate/hexane system)

Sources & evidence

ORD record
ord-7d7f1cc3222a4c269ff044258ef784b8
Source dataset
uspto-grants-2004_09
Patent number
US06790844B2

Reaction notes

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