Nitric Acid → 1,10-Phenanthroline-5,6-dione

HRID 1261810

Reaktionsgleichung

Reaktionsgleichung von HRID 1261810
[N:1]1[C:14]2[C:5](=[CH:6][CH:7]=[C:8]3[C:13]=2[N:12]=[CH:11][CH:10]=[CH:9]3)[CH:4]=[CH:3][CH:2]=1.[Br-].[K+].[OH-:17].[Na+].[N+]([O-])(O)=[O:20]>S(=O)(=O)(O)O>[N:1]1[C:14]2[C:13]3[C:8](=[CH:9][CH:10]=[CH:11][N:12]=3)[C:7](=[O:17])[C:6](=[O:20])[C:5]=2[CH:4]=[CH:3][CH:2]=1

Komponenten

6

Edukt 4

HCID 944Nitric AcidHCID 13181,10-PhenanthrolineHCID 14798Sodium HydroxideHCID 253877Potassium Bromide

Produkt 1

HCID 728101,10-Phenanthroline-5,6-dioneAusbeute 67 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1118Sulfuric AcidLösungsmittel

Reaktionsbedingungen

Temperatur
40 °C

Versuchsvorschrift

1,10-phenanthroline (10.0 g, 55.5 mmol) and potassium bromide (15.0 g, 126 mmol) were in 250 ml two-neck bottle and the outlet of the condenser tube was introduced with a rubber pipe into NaOH aqueous solution. Sulfuric acid (100 mL, 98%) was poured under ice bath condition, and then fuming nitric acid (50.0 mL, 68% w/w) was added after removing ice bath. Then, the temperature was increased to 40° C. for three hours and further increased to 80˜90° C. for one hour. And then, the temperature decreased and the condenser tube was removed, waiting for the dispersion of bromine gas which remained in the bottle. After 1˜2 hours, the solution in the bottle was poured into ice water and NaOH aqueous solution was added slowly until pH of the mixed solution reached 6˜7. At this time, a large number of yellow solid precipitations were produced, filtered with clean water and then collected as products. Finally, the yellow solids of 7.81 g with a yield of 67% were obtained by recrystallizing the said products with methanol.

Aufarbeitung

  1. customafter removing ice bath
  2. temperaturefurther increased to 80˜90° C. for one hour
  3. customthe condenser tube was removed
  4. waitwaiting for the dispersion of bromine gas which
  5. waitAfter 1˜2 hours
  6. additionthe solution in the bottle was poured into ice water and NaOH aqueous solution
  7. additionwas added slowly until pH of the mixed solution
  8. customAt this time, a large number of yellow solid precipitations
  9. customwere produced
  10. filtrationfiltered with clean water
  11. customcollected as products
  12. customFinally, the yellow solids of 7.81 g with a yield of 67% were obtained
  13. customby recrystallizing the said products with methanol

Quellen und Nachweise

ORD-Eintrag
ord-3eb7490d4ede4a25a3d7acf2f5d48483
Quelldatensatz
uspto-grants-2013_06
Patentnummer
US08471037B2

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