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

HRID 1589903

Reaction equation

HRID 1589903 reaction equation
[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

Participants

5

Reactant 2

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

Product 1

HCID 6214835,12-Naphthacenedione, 1,2,3,4-tetrahydro-Yield 147.4%

Reagents, catalysts & solvents 2

HCID 67752,3-Dichloro-5,6-dicyano-1,4-benzoquinoneCatalystHCID 180AcetoneSolvent2×

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-c84cee397ca749b6b170a15531a540b2
Source dataset
uspto-grants-1993_04
Patent number
US05200513

Linked notes

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