Water → 5-Nitro-N-(4-pyridinyl)-1H-indol-1-amine hydrochloride

HRID 1708130Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1708130
[N+:1]([C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[N:9]([NH2:13])[CH:8]=[CH:7]2)([O-:3])=[O:2].Cl.[Cl:15][C:16]1[CH:21]=[CH:20][N:19]=[CH:18][CH:17]=1.O.C(=O)([O-])[O-].[Na+].[Na+]>C(O)(C)C>[ClH:15].[N+:1]([C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[N:9]([NH:13][C:16]1[CH:21]=[CH:20][N:19]=[CH:18][CH:17]=1)[CH:8]=[CH:7]2)([O-:3])=[O:2]

Komponenten

6

Edukt 4

HCID 962WaterHCID 10340Sodium CarbonateHCID 818524-Chloropyridine hydrochloride2×HCID 105834305-nitro-1H-indol-1-amine

Produkt 1

HCID 190724035-Nitro-N-(4-pyridinyl)-1H-indol-1-amine hydrochlorideAusbeute 51,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 3776IsopropanolLösungsmittel

Versuchsvorschrift

A solution of 5-nitro-1H-indol-1-amine (4.5 g) and 4-chloropyridine hydrochloride (4.5 g) in 175 ml of isopropanol was stirred at reflux for two hours, another equivalent of 4-chloropyridine hydrochloride was added and the mixture was refluxed for two additional hours. The reaction mixture was then cooled, stirred with water, basified with sodium carbonate and extracted with ethyl acetate. The organic extract was washed with water and saturated sodium chloride solution, was dried (MgSO4), filtered and concentrated to 9 g of dark oil. This oil was purified by flash chromatography (silica, ethyl acetate) to give 3.8 g of light brown solid, m.p. 183°-184° . This material was converted to the hydrochloride salt and recrystallized twice from methanol/ether to give 3.5 g of orange needles, m.p. 300°-302° (dec.).

Aufarbeitung

  1. temperatureat reflux for two hours
  2. temperaturethe mixture was refluxed for two additional hours
  3. temperatureThe reaction mixture was then cooled
  4. extractionextracted with ethyl acetate
  5. extractionThe organic extract
  6. washwas washed with water and saturated sodium chloride solution
  7. dry with materialwas dried (MgSO4)
  8. filtrationfiltered
  9. concentrationconcentrated to 9 g of dark oil
  10. customThis oil was purified by flash chromatography (silica, ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-a5700c32547f45bb8f976ef8881cf6d8
Quelldatensatz
uspto-grants-1994_10
Patentnummer
US05356910

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