Hydrochloric Acid → Isoquinoline-6-sulfonyl chloride

HRID 1845941노트

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HRID 1845941 반응식
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>[Cl:35][S:16]([C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH:8]=[N:7][CH:6]=[CH:5]2)(=[O:19])=[O:17]

참가 물질

10

반응물 7

HCID 313Hydrochloric AcidHCID 1099SulfiteHCID 1118Sulfuric AcidHCID 516892Sodium BicarbonateHCID 5889916-Aminoisoquinoline2회HCID 23665763Sodium BisulfiteHCID 23668193Sodium Nitrite

생성물 1

HCID 55280287Isoquinoline-6-sulfonyl chloride

시약·촉매·용매 2

HCID 24014Cupric Chloride촉매HCID 176Acetic Acid용매

실험 절차

4.0 g of 6-aminoisoquinoline (Reference Compound 1) was suspended at 0° C. in 40 mL of concentrated hydrochloric acid (35%). 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 organic layer was washed with saturated saline and then dried over anhydrous sodium sulfate. The obtained dichloromethane solution was used in the next reaction without being further purified because the compound of interest was unstable.

후처리

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

출처 및 근거

ORD 기록
ord-21efcbfafd874fd48576390005063c52
출처 데이터셋
uspto-grants-2015_02
특허 번호
US08951997B2

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