Sulfuryl chloride → 5-Chloroisoquinolin-6-ol

HRID 1887065Notes

Reaction equation

HRID 1887065 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-48b531481f4345008bd0167d66546324
Source dataset
uspto-grants-2013_08
Patent number
US08501736B2

Reaction notes

Loading…