p-Toluidine → 2-Chloro-3-(4-methylanilino)naphthalene-1,4-dione

HRID 1895500

Reaktionsgleichung

Reaktionsgleichung von HRID 1895500
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([CH3:8])=[CH:4][CH:3]=1.Cl[C:10]1[C:11](=[O:22])[C:12]2[C:17]([C:18](=[O:21])[C:19]=1[Cl:20])=[CH:16][CH:15]=[CH:14][CH:13]=2>C(O)C>[Cl:20][C:19]1[C:18](=[O:21])[C:17]2[C:12]([C:11](=[O:22])[C:10]=1[NH:1][C:2]1[CH:7]=[CH:6][C:5]([CH3:8])=[CH:4][CH:3]=1)=[CH:13][CH:14]=[CH:15][CH:16]=2

Komponenten

4

Edukt 2

HCID 7813p-ToluidineHCID 8342Dichlone

Produkt 1

HCID 2658672-Chloro-3-(4-methylanilino)naphthalene-1,4-dione

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

p-Toluidin (1.4 g, 13.2 mmol) was added to the solution of 2,3-dichloro-1,4-naphthoquinone (1.0 g, 4.4 mmol) in ethanol (300 ml). The reaction mixture was allowed to stir at room temperature for over night. The precipitated product was filtered off and washed with cold ethanol. The product was purified by recrystallization with ethanol/CHCl3 (1:5) to afford the fine reddish needles. Yield: 0.642 g (53.8%), Mp: 295° C.

Aufarbeitung

  1. filtrationThe precipitated product was filtered off
  2. washwashed with cold ethanol
  3. customThe product was purified by recrystallization with ethanol/CHCl3 (1:5)
  4. customto afford the fine reddish needles

Quellen und Nachweise

ORD-Eintrag
ord-7228c457586d490a86004de5e007d223
Quelldatensatz
uspto-grants-2013_08
Patentnummer
US08513437B2

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