Sodium Hydroxide → 5,7-Dichloro-6-fluoro-isoquinoline

HRID 2370739Notes

Reaction equation

HRID 2370739 reaction equation
[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][N:8]=[CH:9]2)=[CH:4][C:3]=1[F:12].[Cl:13]N1C(=O)CCC1=O.[OH-].[Na+]>S(=O)(=O)(O)O>[Cl:13][C:4]1[C:3]([F:12])=[C:2]([Cl:1])[CH:11]=[C:10]2[C:5]=1[CH:6]=[CH:7][N:8]=[CH:9]2

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 31398Chlorosuccinimide3×HCID 534189227-Chloro-6-fluoroisoquinoline

Product 1

HCID 576468095,7-Dichloro-6-fluoro-isoquinolineYield 21.8%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Conditions

Temperature
50 °C

Procedure

5 g (23.1 mmol) 7-Chloro-6-fluoro-isoquinoline (6) were dissolved in 90 ml conc. sulfuric acid. At room temperature 7.34 g (55 mmol) N-chlorosuccinimide were added. The solution was heated to 50° C. and another 3.67 g (27.5 mmol) N-chlorosuccinimide were added. After standing overnight at room temperature, the reaction was again heated to 50° C. and another 18.35 g (137.5 mmol) N-chlorosuccinimide were added during the next 8 h. For working up, the reaction mixture was poured on ice. The aqueous solution was adjusted to alkaline pH with sodium hydroxide. The precipitate was filtered off and extracted three times with dichloromethane. The dichloromethane phases were dried with magnesium sulfate and evaporated to yield 1.09 g of the title compound, which was used without further purification.

Workup

  1. temperaturethe reaction was again heated to 50° C.
  2. additionthe reaction mixture was poured on ice
  3. filtrationThe precipitate was filtered off
  4. extractionextracted three times with dichloromethane
  5. dry with materialThe dichloromethane phases were dried with magnesium sulfate
  6. customevaporated

Sources & evidence

ORD record
ord-988a3d8be41946aeabaa7e71ce375825
Source dataset
uspto-grants-2014_04
Patent number
US08710228B2

Reaction notes

Loading…