Ammonia → HCID 58310529, compound

HRID 1256188Notes

Reaction equation

HRID 1256188 reaction equation
[Br:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6](Cl)=[CH:7][CH:8]=[N:9]2)=[N:4][CH:3]=1.[NH3:13].O>O1CCOCC1>[Br:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6]([NH2:13])=[CH:7][CH:8]=[N:9]2)=[N:4][CH:3]=1

Participants

5

Reactant 3

HCID 222AmmoniaHCID 962WaterHCID 134591373-Bromo-8-chloro-1,5-naphthyridine

Product 1

HCID 58310529HCID 58310529, compoundYield 76.6%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
160 °C

Procedure

In a sealed reactor, 500 mg (2.04 mmol, 1 eq) of 7-bromo-4-chloro-1,5-naphthyridine (G. B. Barlin et al. Aust. J. Chem. 1985, 38, 459-465) and 12 mL (71.3 mmol, 35 eq) of 20% aqueous ammonia solution were introduced in 12 mL of dioxane. The mixture was stirred at 160° C. for 24 h. The mixture was allowed to reach rt and water was added. Aqueous layer was extracted with ethyl acetate. Organic layers were dried over Na2SO4, filtered and evaporated to dryness. The residue was purified by column chromatography using methylene chloride and then methylene chloride/ethanol: 98/2 as eluent. The solvent was evaporated to dryness to afford 350 mg of white powder with 76% yield.

Workup

  1. customto reach rt
  2. extractionAqueous layer was extracted with ethyl acetate
  3. dry with materialOrganic layers were dried over Na2SO4
  4. filtrationfiltered
  5. customevaporated to dryness
  6. customThe residue was purified by column chromatography
  7. customThe solvent was evaporated to dryness

Sources & evidence

ORD record
ord-f7483393e48b4b648494118b5c11a7c5
Source dataset
uspto-grants-2013_06
Patent number
US08461178B2

Reaction notes

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