Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Ammonia | HCID 222 | — |
| Reactant | Water | HCID 962 | — |
| Reactant | 3-Bromo-8-chloro-1,5-naphthyridine | HCID 13459137 | — |
| Solvent | 1,4-Dioxane | HCID 31275 | — |
| Product | HCID 58310529 | HCID 58310529 | 76.6% |
Reaction Steps
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.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08461178B2 |
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| Source dataset | uspto-grants-2013_06 |
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| ORD ID | ord-f7483393e48b4b648494118b5c11a7c5 |
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| Source note | uspto-grants-2013_06 |
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