Ammonia → 7-Bromo-1,5-naphthyridin-2-amine

HRID 1256184Notes

Reaction equation

HRID 1256184 reaction equation
[Br:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][C:8](Cl)=[N:9]2)=[N:4][CH:3]=1.[NH3:13].O>O1CCOCC1>[Br:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][C:8]([NH2:13])=[N:9]2)=[N:4][CH:3]=1

Participants

5

Reactant 3

HCID 222AmmoniaHCID 962WaterHCID 583105447-Bromo-2-chloro-1,5-naphthyridine

Product 1

HCID 583105327-Bromo-1,5-naphthyridin-2-amineYield 80%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
160 °C

Procedure

In a sealed reactor, 500 mg (1.23 mmol, 1 eq) of 7-bromo-2-chloro-1,5-naphthyridine and 7 mL (41.6 mmol, 33 eq) of 20% aqueous ammonia solution were introduced in 7 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 220 mg of white powder with 80% 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-6b8b6c9b669a4c45981c5dbd5658792a
Source dataset
uspto-grants-2013_06
Patent number
US08461178B2

Reaction notes

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