Hydrochloric Acid → 5-(5-Isoquinolylsulfanyl)isoquinoline

HRID 619747ノート

反応式

HRID 619747 の反応式
Cl.N[C:3]1[CH:12]=[CH:11][CH:10]=[C:9]2[C:4]=1[CH:5]=[CH:6][N:7]=[CH:8]2.[N-]=[N+]=[N-].[Na+].C([O-])(=O)C.[Na+].[OH-].[Na+].[CH:24]1[C:33]2[CH:32]=[CH:31][CH:30]=[C:29]([SH:34])[C:28]=2[CH:27]=[CH:26][N:25]=1>C(OCC)(=O)C.O>[CH:8]1[C:9]2[C:4](=[C:3]([S:34][C:29]3[CH:30]=[CH:31][CH:32]=[C:33]4[C:28]=3[CH:27]=[CH:26][N:25]=[CH:24]4)[CH:12]=[CH:11][CH:10]=2)[CH:5]=[CH:6][N:7]=1

参加物

9

反応物 6

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 33557Sodium AzideHCID 707665-AminoisoquinolineHCID 517045Sodium AcetateHCID 110519635-Isoquinolinethiol

生成物 1

HCID 218469735-(5-Isoquinolylsulfanyl)isoquinoline収率 11.6%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
0 °C

実験手順

To an aqueous 4N hydrochloric acid solution 24 ml of 5-aminoisoquinoline 1.00 g (6.9 mmol), a water solution 2 ml of sodium azide 480 mg (6.9 mmol) was added dropwise. The reaction mixture was stirred at 0° C. for 30 minutes and neutralized with sodium acetate, and insoluble materials were filtered. The filtrate was added to a sodium hydroxide solution (300 mg/3 ml) of 5-isoquinolinethiol 1.23 g (7.6 mmol), and the mixture was stirred for 1.5 hours at 80° C. After adding ethyl acetate, the reaction solution was washed with 1N sodium hydroxide and saturated sodium chloride, and dried over anhydrous magnesium sulfate. The organic layer was concentrated under reduced pressure, the resulting residue was purified by silica gel column chromatography (ethyl acetate), and 5-(5-isoquinolylsulfanyl)isoquinoline 230 mg (11.5%) was obtained.

後処理

  1. filtrationwere filtered
  2. stirringthe mixture was stirred for 1.5 hours at 80° C
  3. washthe reaction solution was washed with 1N sodium hydroxide and saturated sodium chloride
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationThe organic layer was concentrated under reduced pressure
  6. customthe resulting residue was purified by silica gel column chromatography (ethyl acetate)

出典と根拠

ORDレコード
ord-e91e54707b5f44f1aa3b1a0c322e892f
出典データセット
uspto-grants-1999_09
特許番号
US05959107

反応ノート

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