Dichloromethane → 3,4-Dihydroisoquinoline

HRID 726524

反応式

HRID 726524 の反応式
[CH2:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][CH2:3][NH:2]1.C(Cl)Cl.S(OOS([O-])(=O)=O)([O-])(=O)=O.[K+].[K+].[OH-].[Na+]>O.O.O.O.O.O.O.S([O-])([O-])(=O)=O.[Ni+2]>[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][CH2:3][N:2]=1

参加物

7

反応物 4

HCID 6344DichloromethaneHCID 70461,2,3,4-TetrahydroisoquinolineHCID 14798Sodium HydroxideHCID 24412Potassium Persulfate

生成物 1

HCID 767053,4-Dihydroisoquinoline

試薬・触媒・溶媒 2

HCID 5284429Nickel sulfate hexahydrate触媒HCID 962Water溶媒2 回

実験手順

Into a 5000 ml, 3-neck round-bottom flask equipped with a mechanical stirrer is placed 1,2,3,4-tetrahydroisoquinoline (1) (25.005 g) and methylene chloride (750 ml). A solution of potassium persulfate (71.376 g) and sodium hydroxide (18.0456 g) in deionized water (1650 ml) is added. While vigorously stirring the biphasic mixture, a solution of nickel sulfate hexahydrate (0.6499 g) in deionized water (75 ml) is added dropwise to the mixture. The reaction is allowed to stir overnight at room temperature. The biphasic mixture is vacuum filtered through Celite, the phases separated and the water layer extracted (3×300 ml) with methylene chloride. The organics are combined, dried with MgSO4 and reduced by rotary evaporation to a thick, dark brown oil. The desired product is isolated from the oil by Kugelrohr distillation (0.1 mm Hg, 75° C.). The preparation is represented by the following reaction: ##STR26##

後処理

  1. customInto a 5000 ml, 3-neck round-bottom flask equipped with a mechanical stirrer
  2. stirringto stir overnight at room temperature
  3. filtrationfiltered through Celite
  4. customthe phases separated
  5. extractionthe water layer extracted (3×300 ml) with methylene chloride
  6. dry with materialdried with MgSO4
  7. customreduced by rotary evaporation to a thick, dark brown oil

出典と根拠

ORDレコード
ord-866a01512fa14a7a81855cbc5990170c
出典データセット
uspto-grants-1998_01
特許番号
US05710116

関連ノート

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