Hydrochloric Acid → {2-[(3-Nitropyridin-2-yl)amino]phenyl}(phenyl)methanone

HRID 1633352Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1633352
[NH2:1][C:2]1[CH:15]=[CH:14][CH:13]=[CH:12][C:3]=1[C:4]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)=[O:5].Cl[C:17]1[C:22]([N+:23]([O-:25])=[O:24])=[CH:21][CH:20]=[CH:19][N:18]=1.Cl>>[N+:23]([C:22]1[C:17]([NH:1][C:2]2[CH:15]=[CH:14][CH:13]=[CH:12][C:3]=2[C:4]([C:6]2[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=2)=[O:5])=[N:18][CH:19]=[CH:20][CH:21]=1)([O-:25])=[O:24]

Komponenten

4

Edukt 3

HCID 313Hydrochloric AcidHCID 760802-AminobenzophenoneHCID 796132-Chloro-3-nitropyridine

Produkt 1

HCID 13388384{2-[(3-Nitropyridin-2-yl)amino]phenyl}(phenyl)methanone

Versuchsvorschrift

A mixture of 56.0 g (0.28 mole) of 2-aminobenzophenone and 49.6 g (0.31 mole) of 2-chloro-3-nitropyridine was heated by means of an oil bath with stirring at 150° C. for 45 minutes (evolution of hydrogen chloride gas ceased). The product was partitioned between 130 ml of methylene chloride and 250 ml aqueous bicarbonate solution. The aqueous layer was extracted three times with 50 ml portions of methylene chloride. All methylene chloride solutions were combined and dried over sodium sulfate and filtered. Methylene chloride was stripped off in a rotary vacuum evaporator to give a dark brown viscous oil. The product was purified by column chromatography, eluting with methylene chloride on silica gel. On evaporation of the methylene chloride, an orange oil was obtained which crystallized slowly. The crystals were triturated in 105 ml of 1:1 tert-butyl alcohol/petroleum ether (30→60). Crystalline yellow solid, 50.5 g (58%) was obtained by contrifuging and drying, m.p. 85° C.

Aufarbeitung

  1. temperaturewas heated by means of an oil bath
  2. customThe product was partitioned between 130 ml of methylene chloride and 250 ml aqueous bicarbonate solution
  3. extractionThe aqueous layer was extracted three times with 50 ml portions of methylene chloride
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. customMethylene chloride was stripped off in a rotary vacuum evaporator
  7. customto give a dark brown viscous oil
  8. customThe product was purified by column chromatography
  9. washeluting with methylene chloride on silica gel
  10. customOn evaporation of the methylene chloride
  11. customan orange oil was obtained which
  12. customcrystallized slowly
  13. customThe crystals were triturated in 105 ml of 1:1 tert-butyl alcohol/petroleum ether (30→60)
  14. customCrystalline yellow solid, 50.5 g (58%) was obtained
  15. customdrying

Quellen und Nachweise

ORD-Eintrag
ord-69b79639805342e3bb7d64692f6f99da
Quelldatensatz
uspto-grants-1984_10
Patentnummer
US04480100

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