2,6-Dihydroxyanthraquinone → 2-(Diethylamino)ethoxy anthraquinone

HRID 616341

反応式

HRID 616341 の反応式
O[C:2]1[CH:15]=[CH:14][C:13]2[C:12](=[O:16])[C:11]3[C:6](=[CH:7][CH:8]=[C:9](O)[CH:10]=3)[C:5](=[O:18])[C:4]=2[CH:3]=1.ClC1C=CC=CC=1.Cl.[CH2:27]([N:29]([CH2:33][CH3:34])[CH2:30][CH2:31]Cl)[CH3:28].[OH-:35].[K+]>C(Cl)(Cl)Cl.O>[CH2:27]([N:29]([CH2:33][CH3:34])[CH2:30][CH2:31][O:35][C:10]1[C:11]2[C:12](=[O:16])[C:13]3[C:4](=[CH:3][CH:2]=[CH:15][CH:14]=3)[C:5](=[O:18])[C:6]=2[CH:7]=[CH:8][CH:9]=1)[CH3:28]

参加物

7

反応物 4

HCID 67762,6-DihydroxyanthraquinoneHCID 7964ChlorobenzeneHCID 133631-Chloro-2-(diethylamine)ethane hydrochlorideHCID 14797Potassium Hydroxide

生成物 1

HCID 4121832-(Diethylamino)ethoxy anthraquinone

試薬・触媒・溶媒 2

HCID 962Water溶媒2 回HCID 6212Chloroform溶媒

実験手順

In addition to the methods given in Examples 1 and 2, the following method has also proven useful. To a mixture of 114g (0.6 mole) of 2,6-dihydroxyanthraquinone and 1.2 liters of chlorobenzene was added a solution of 412g (2.4 moles) 2-diethylaminoethyl chloride hydrochloride in 350 ml. of water. With efficient stirring, a solution of 264g (4.0 moles) of potassium hydroxide pellets (85%) in 350 ml. of water was added. The resulting mixture was heated with continued stirring on a steam bath for about 24 hours, then cooled by adding about 500 g of ice. 400 ml. chloroform was added. The lower organic layer was separated and washed several times with water, then dried with anhydrous magnesium sulfate. After filtration, the solvents were removed under reduced pressure in a rotary evaporator. The residue was recrystallized from a mixture of methanol and chloroform as described in Example 1 to give 2,6-bis 2-(diethylamino)ethoxy anthraquinone base, M.P. 178-181° C. The base can be converted to the dihydrochloride salt as described in Example 1.

後処理

  1. additionIn addition to the methods
  2. temperatureThe resulting mixture was heated
  3. temperaturecooled
  4. customThe lower organic layer was separated
  5. washwashed several times with water
  6. dry with materialdried with anhydrous magnesium sulfate
  7. filtrationAfter filtration
  8. customthe solvents were removed under reduced pressure in a rotary evaporator
  9. customThe residue was recrystallized from a mixture of methanol and chloroform

出典と根拠

ORDレコード
ord-258b699b381044cf9af7deada2d9a7dd
出典データセット
uspto-grants-1978_02
特許番号
US04073904

関連ノート

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