1-Amino-2-methylanthraquinone → 1-Amino-4-bromo-2-methylanthraquinone

HRID 1413203

Reaktionsgleichung

Reaktionsgleichung von HRID 1413203
[NH2:1][C:2]1[C:15]2[C:14](=[O:16])[C:13]3[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=3)[C:7](=[O:17])[C:6]=2[CH:5]=[CH:4][C:3]=1[CH3:18].[Br:19]Br>CC(O)=O>[NH2:1][C:2]1[C:15]2[C:14](=[O:16])[C:13]3[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=3)[C:7](=[O:17])[C:6]=2[C:5]([Br:19])=[CH:4][C:3]=1[CH3:18]

Komponenten

4

Edukt 2

HCID 67021-Amino-2-methylanthraquinoneHCID 24408Bromine

Produkt 1

HCID 664801-Amino-4-bromo-2-methylanthraquinoneAusbeute 90 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 176Acetic AcidLösungsmittel

Reaktionsbedingungen

Temperatur
40 °C

Versuchsvorschrift

1-amino-2-methylanthraquinone (300 g) is slurried with 1500 ml of HOAc in a 5-liter flask. The temperature is raised to 40° C. Neat bromine (405 g) is added over 21/2 hours with stirring at 40°-50° C. The mixture is stirred for 20 additional minutes and filtered. The solids so recovered are washed with HOAc and water and sucked dry with an aspirator and transferred to a reaction flask along with 150 g of NaHSO3 and 1.5 liters of water. The mixture is gradually heated to 90° C. (over two hours) with stirring to give 1-amino-2-methyl-4-bromoanthraquinone as a solid which is recovered from the reaction mixture by filtration in 90% yield, rinsed with water and dried overnight at 155° C. and 1 mm Hg absolute vacuum.

Aufarbeitung

  1. stirringThe mixture is stirred for 20 additional minutes
  2. filtrationfiltered
  3. customThe solids so recovered
  4. washare washed with HOAc and water
  5. customsucked dry with an aspirator
  6. customtransferred to a reaction flask along with 150 g of NaHSO3 and 1.5 liters of water
  7. temperatureThe mixture is gradually heated to 90° C. (over two hours)
  8. stirringwith stirring

Quellen und Nachweise

ORD-Eintrag
ord-9595e9a652524ffa867f4380e14dfd5a
Quelldatensatz
uspto-grants-1981_02
Patentnummer
US04249007

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