Sulfuryl chloride → 5-Chloroisoquinolin-6-ol

HRID 1022854Notes

Reaction equation

HRID 1022854 reaction equation
S(Cl)([Cl:4])(=O)=O.[OH:6][C:7]1[CH:8]=[C:9]2[C:14](=[CH:15][CH:16]=1)[CH:13]=[N:12][CH:11]=[CH:10]2>ClCCl.C(OCC)C>[Cl:4][C:8]1[C:7]([OH:6])=[CH:16][CH:15]=[C:14]2[C:9]=1[CH:10]=[CH:11][N:12]=[CH:13]2

Participants

5

Reactant 2

HCID 24648Sulfuryl chlorideHCID 135483582Isoquinolin-6-ol

Product 1

HCID 1357421835-Chloroisoquinolin-6-olYield 89%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherCatalystHCID 6344DichloromethaneSolvent

Procedure

0.61 mL (1.02 g, 7.6 mmol) of sulfuryl chloride were added to a solution of 1.0 g (6.9 mmol) of compound 7 in 30 mL of dichloromethane. Three drops diethyl ether were added and the reaction was stirred at room temperature for 5 h. The solvents were removed by distillation and the remainder was treated with aqueous NaHCO3 solution. The precipitate was filtered, washed with water and dried to give 1.1 g (89%) of compound 8 as a green-yellow solid.

Workup

  1. customThe solvents were removed by distillation
  2. additionthe remainder was treated with aqueous NaHCO3 solution
  3. filtrationThe precipitate was filtered
  4. washwashed with water
  5. customdried

Sources & evidence

ORD record
ord-e0327da39f6544cda9c19cd9f7eb9932
Source dataset
uspto-grants-2014_05
Patent number
US08722671B2

Reaction notes

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