Sulfuryl chloride → 5-Chloroisoquinolin-6-ol

HRID 2370716Notes

Reaction equation

HRID 2370716 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 6-hydroxy-isoquinoline 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 1 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-4465983dc7034bf1b8772db3becb061d
Source dataset
uspto-grants-2014_04
Patent number
US08710228B2

Reaction notes

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