Hydrochloric Acid → HCID 612005, Verbindung

HRID 1603849

Reaktionsgleichung

Reaktionsgleichung von HRID 1603849
Cl[C:2]1[CH:7]=[CH:6][N:5]=[CH:4][C:3]=1[N+:8]([O-:10])=[O:9].[NH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.Cl>O.COCCO>[C:12]1([NH:11][C:2]2[CH:7]=[CH:6][N:5]=[CH:4][C:3]=2[N+:8]([O-:10])=[O:9])[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Komponenten

5

Edukt 3

HCID 313Hydrochloric AcidHCID 6115AnilineHCID 27357814-Chloro-3-nitropyridine

Produkt 1

HCID 612005HCID 612005, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 22504935Water 2-methoxyethanolLösungsmittel

Versuchsvorschrift

A solution of 4-chloro-3-nitropyridine (II: R'=4-aza, halogen=Cl) (3.22 g, 0.020 mol), aniline (III: R1' =H) (1.85 mL, 0.020 mol) and conc. HCl (0.17 mL, 0.02 mol) in 1:1 water/2-methoxyethanol (40 mL) was refluxed for 18 hours, then concentrated to dryness. The residue was partitioned between saturated aqueous NaHCO3 and EtOAc, and the organic portion was worked up to give an oil which was chromatographed on silica gel. Petroleum ether eluted foreruns, while EtOAc/petroleum ether (1:1) gave 4-(N-phenylamino)-3-nitropyridine (VI: R'=4-aza, R1'=H) (2.02 g, 41%); mp (EtOAc/petroleum ether) 119° C.

Aufarbeitung

  1. concentrationconcentrated to dryness
  2. customThe residue was partitioned between saturated aqueous NaHCO3 and EtOAc
  3. customto give an oil which
  4. customwas chromatographed on silica gel

Quellen und Nachweise

ORD-Eintrag
ord-059b58db1bc043a792c17ae3054ad7e7
Quelldatensatz
uspto-grants-1999_11
Patentnummer
US05990146

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