Ammonium cerium-nitrate → 5,12-Naphthacenedione, 1,2,3,4-tetrahydro-

HRID 1589903

Reaktionsgleichung

Reaktionsgleichung von HRID 1589903
[CH2:1]1[C:18]2[CH:5]([CH2:6][CH:7]3[CH:16]([CH:17]=2)[C:15](=[O:19])[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[CH2:8]3)[CH2:4][CH2:3][CH2:2]1.[N+]([O-])([O-])=[O:21].[NH4+].[Ce]>CC(C)=O.ClC1C(=O)C(C#N)=C(C#N)C(=O)C=1Cl>[CH2:13]1[C:14]2[C:15](=[O:19])[C:16]3[C:7](=[CH:6][C:5]4[C:18]([CH:17]=3)=[CH:1][CH:2]=[CH:3][CH:4]=4)[C:8](=[O:21])[C:9]=2[CH2:10][CH2:11][CH2:12]1

Komponenten

5

Edukt 2

HCID 57418452Ammonium cerium-nitrateHCID 67719023Octahydro-11-naphthacenone

Produkt 1

HCID 6214835,12-Naphthacenedione, 1,2,3,4-tetrahydro-Ausbeute 147,4 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 67752,3-Dichloro-5,6-dicyano-1,4-benzoquinoneKatalysatorHCID 180AcetoneLösungsmittel2×

Versuchsvorschrift

A solution of 36 mg (0.075 mmol) of the octahydro-11-naphthacenone and 60 mg (0.675 mmol) of NaHCP3 in 10 mL of acetone was treated with a solution of 167 mg (3mmol) of cerium ammonium nitrate (CAN) and 1 mg of dichlorodicyanobenzoquinone (DDQ) in 2 mL of acetone added in one portion at 0 degrees centigrade. The reaction mixture was stirred at room temperature for 1.5 hours during which the color changed from shiny yellow to orange red, and then 25 mL of CH2Cl2 was added. The mixture was filtered through over Celite. The organic layer was washed with saturated NaCl solution (2×20 mL), dried over Na2SO4, and evaporated to give the tetrahydro-5,12-naphthacenedione as a red crystals (29 mg, 86 percent).mp greater than 258 degrees centigrade (decomp).

Aufarbeitung

  1. additionadded in one portion at 0 degrees centigrade
  2. additionwas added
  3. filtrationThe mixture was filtered through over Celite
  4. washThe organic layer was washed with saturated NaCl solution (2×20 mL)
  5. dry with materialdried over Na2SO4
  6. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-c84cee397ca749b6b170a15531a540b2
Quelldatensatz
uspto-grants-1993_04
Patentnummer
US05200513

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