Water → 4-Chloro-5-(5-isoquinolylsulfanyl)-1,2-benzenediamine

HRID 619730

Reaktionsgleichung

Reaktionsgleichung von HRID 619730
[Cl:1][C:2]1[C:8]([S:9][C:10]2[CH:19]=[CH:18][CH:17]=[C:16]3[C:11]=2[CH:12]=[CH:13][N:14]=[CH:15]3)=[CH:7][C:5]([NH2:6])=[C:4]([N+:20]([O-])=O)[CH:3]=1.O.[OH-].[Na+]>Cl>[Cl:1][C:2]1[CH:3]=[C:4]([NH2:20])[C:5]([NH2:6])=[CH:7][C:8]=1[S:9][C:10]1[CH:19]=[CH:18][CH:17]=[C:16]2[C:11]=1[CH:12]=[CH:13][N:14]=[CH:15]2

Komponenten

5

Edukt 3

HCID 962WaterHCID 14798Sodium HydroxideHCID 218469034-Chloro-5-(5-isoquinolylsulfanyl)-2-nitroaniline

Produkt 1

HCID 218469304-Chloro-5-(5-isoquinolylsulfanyl)-1,2-benzenediamineAusbeute 89,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 313Hydrochloric AcidLösungsmittel

Versuchsvorschrift

4-Chloro-5-(5-isoquinolylsulfanyl)-2-nitroaniline 1.78 g (5.4 mmol) was dissolved in concentrated hydrochloric acid 30 ml, stannous chloride dihydrate 4.30 g (19.1 mmol) was added, and the mixture was stirred overnight at room temperature. The reaction mixture was poured into water, 50% sodium hydroxide was added to alkalize the mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed with water and with saturated sodium chloride, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The resulting residue was recrystallized from ethyl acetate-n-hexane to give 4-chloro-5-(5-isoquinolylsulfanyl)-1,2-benzenediamine 1.45 g (89.5%).

Aufarbeitung

  1. additionwas added
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe organic layer was washed with water and with saturated sodium chloride
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe resulting residue was recrystallized from ethyl acetate-n-hexane

Quellen und Nachweise

ORD-Eintrag
ord-064ef837141c4fd78d5569ce18e1284f
Quelldatensatz
uspto-grants-1999_09
Patentnummer
US05959107

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