Hydrochloric Acid → 4-chloro-N1-phenylbenzene-1,2-diamine

HRID 1079478Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1079478
C(=O)([O-])[O-].[K+].[K+].S(S([O-])=O)([O-])=O.[Na+].[Na+].[CH:15]1[CH:20]=[CH:19][C:18]([NH:21][C:22]2[CH:27]=[CH:26][C:25]([Cl:28])=[CH:24][C:23]=2[N+:29]([O-])=O)=[CH:17][CH:16]=1.Cl.[OH-].[Na+]>C(O)C.O>[CH:15]1[CH:16]=[CH:17][C:18]([NH:21][C:22]2[CH:27]=[CH:26][C:25]([Cl:28])=[CH:24][C:23]=2[NH2:29])=[CH:19][CH:20]=1

Komponenten

8

Edukt 5

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 14798Sodium HydroxideHCID 24489Sodium DithioniteHCID 855114-Chloro-2-nitro-N-phenylaniline

Produkt 1

HCID 2649994-chloro-N1-phenylbenzene-1,2-diamineAusbeute 74,9 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 702EthanolLösungsmittelHCID 962WaterLösungsmittel

Versuchsvorschrift

Potassium carbonate (13 g) and sodium hydrosulphite (11.4 g) were added portionwise over 3 hour to a suspension of 4-chloro-2-nitrodiphenylamine (3.6 g) in 95% ethanol (100 ml) and water (100 ml). The mixture was stirred at 23° for 20 h. The reaction mixture was then acidified to pH=4 with conc. hydrochloric acid (20 ml); then 10% solution of sodium hydroxide (80 ml) was added until pH=10 and the solution extracted with ethyl acetate (2×150 ml). The combined organic extracts were washed with brine (2×150 ml), dried and concentrated in vacuo to give the crude compound as a yellow solid (7.8 g) which was purified by flash chromatography (eluting with CH-EA 90:10 then 70:30) to give the title compound as a yellow foam (2.37 g). Tlc. CH-EA (1:1), Rf 0.66.

Aufarbeitung

  1. extractionthe solution extracted with ethyl acetate (2×150 ml)
  2. washThe combined organic extracts were washed with brine (2×150 ml)
  3. customdried
  4. concentrationconcentrated in vacuo
  5. customto give the crude compound as a yellow solid (7.8 g) which
  6. customwas purified by flash chromatography (
  7. washeluting

Quellen und Nachweise

ORD-Eintrag
ord-430da5b1c62c4d478f312fbfee85b8c2
Quelldatensatz
uspto-grants-1996_12
Patentnummer
US05580895

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