Hydrochloric Acid → Isoquinoline-6-sulfonyl chloride

HRID 333990ノート

反応式

HRID 333990 の反応式
N[C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH:8]=[N:7][CH:6]=[CH:5]2.N([O-])=O.[Na+].[S:16]([O-:19])([O-])=[O:17].S(=O)(O)[O-].[Na+].S(=O)(=O)(O)O.C(=O)(O)[O-].[Na+].[ClH:35]>[Cu](Cl)Cl.C(O)(=O)C>[CH:8]1[C:9]2[C:4](=[CH:3][C:2]([S:16]([Cl:35])(=[O:19])=[O:17])=[CH:11][CH:10]=2)[CH:5]=[CH:6][N:7]=1

参加物

10

反応物 7

HCID 313Hydrochloric AcidHCID 1099SulfiteHCID 1118Sulfuric AcidHCID 516892Sodium BicarbonateHCID 5889916-AminoisoquinolineHCID 23665763Sodium BisulfiteHCID 23668193Sodium Nitrite

生成物 1

HCID 55280287Isoquinoline-6-sulfonyl chloride

試薬・触媒・溶媒 2

HCID 24014Cupric Chloride触媒HCID 176Acetic Acid溶媒

反応条件

温度
0 °C

実験手順

4.0 g of commercially available 6-aminoisoquinoline was suspended in 40 mL of concentrated hydrochloric acid (35%) with cooling at 0° C. To the suspension, 4.0 g of sodium nitrite was added in small portions, and the mixture was stirred for 30 minutes. This reaction solution was added dropwise at 0° C. to a mixed solution of 20 mL of acetic acid saturated with sulfite gas generated from sodium bisulfite and sulfuric acid, and 298 mg of copper chloride, and the mixture was stirred for 1 hour. The mixture was neutralized by the addition of a saturated aqueous solution of sodium bicarbonate, followed by extraction with dichloromethane (100 mL×2). The obtained organic layer was washed with saturated saline and then dried over anhydrous sodium sulfate. A dichloromethane solution obtained by filtration was used in the next reaction without being further purified because the compound of interest was unstable.

後処理

  1. stirringthe mixture was stirred for 1 hour
  2. extractionfollowed by extraction with dichloromethane (100 mL×2)
  3. washThe obtained organic layer was washed with saturated saline
  4. dry with materialdried over anhydrous sodium sulfate
  5. customA dichloromethane solution obtained by filtration
  6. customwas used in the next reaction
  7. customwithout being further purified because the compound of interest

出典と根拠

ORDレコード
ord-06d43ef930574f218e847d9d08bfe332
出典データセット
uspto-grants-2014_11
特許番号
US08883792B2

反応ノート

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