Ammonia → 2-Amino-5-[4'-(amino)anilino]-1,4-benzoquinone

HRID 2398015Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2398015
[NH2:1][C:2]1[CH:3]=[C:4]([OH:10])[CH:5]=[CH:6][C:7]=1[O:8]C.N.OO.Cl.Cl.[C:16]1([NH2:23])[CH:21]=[CH:20][C:19]([NH2:22])=[CH:18][CH:17]=1>CC(C)=O.O>[NH2:1][C:2]1[C:7](=[O:8])[CH:6]=[C:5]([NH:22][C:19]2[CH:20]=[CH:21][C:16]([NH2:23])=[CH:17][CH:18]=2)[C:4](=[O:10])[CH:3]=1

Komponenten

7

Edukt 4

HCID 222AmmoniaHCID 784Hydrogen PeroxideHCID 122051,4-Diaminobenzene dihydrochlorideHCID 203418413-Amino-4-methoxyphenol

Produkt 1

HCID 234675252-Amino-5-[4'-(amino)anilino]-1,4-benzoquinone

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 180AcetoneLösungsmittelHCID 962WaterLösungsmittel

Versuchsvorschrift

0.75 mole (10.5 g) of 3-amino-4-methoxy phenol is dissolved in 50 cc of acetone to which have been added 50 cc of ammonia (22° Be) and 250 cc of H2O2 (20 volumes). To this solution there is immediately added 0.05 mole (9.0 g) of paraphenylene diamine dihydrochloride in solution in 100 cc of water. The resulting reaction mixture is agitated for two hours at ambient temperature at which time the reaction mixture is filtered to recover the precipitate which has formed. After recrystallizing the precipitate in ethylacetate and washing the recrystallized product initially with a little methyl cellosolve and then with a little ether, 2-amino-5-[4'-(amino)anilino]-1,4-benzoquinone is obtained which is chromatographically pure and which melts with decomposition above 260° C.

Aufarbeitung

  1. customThe resulting reaction mixture
  2. filtrationis filtered
  3. customto recover the precipitate which
  4. customhas formed
  5. customAfter recrystallizing the precipitate in ethylacetate
  6. washwashing the recrystallized product initially with a little methyl cellosolve

Quellen und Nachweise

ORD-Eintrag
ord-6c52f6597c064dac9f32ba30a2e61011
Quelldatensatz
uspto-grants-1977_05
Patentnummer
US04023926

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