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

HRID 1589903

反応式

HRID 1589903 の反応式
[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

参加物

5

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 67752,3-Dichloro-5,6-dicyano-1,4-benzoquinone触媒HCID 180Acetone溶媒2 回

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-c84cee397ca749b6b170a15531a540b2
出典データセット
uspto-grants-1993_04
特許番号
US05200513

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