Sodium Hydroxide → 5,7-Dichloro-6-fluoro-isoquinoline
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]2Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 50 °C
Procedure
5.0 g (27.5 mmol) 7-Chloro-6-fluoro-isoquinoline (150) were dissolved in 90 ml of conc. sulphuric acid. At room temperature 7.35 g (55.0 mmol) N-Chlorosuccinimide were added and the mixture was stirred at 50° C. After standing overnight at room temperature another 3 eq. N-Chlorosuccinimide were added and at the following again 5 eq. N-Chlorosuccinimide were added and the temperature was increased to 80° C. After no further conversion could be detected, the mixture was cooled to room temperature and poured on ice. The aqueous solution was brought to basic pH by adding solid NaOH. The precipitate was filtered off and washed three times with dichloromethane. After drying the organic filtrates with MgSO4 and evaporation of the solvent 1.09 g of the desired isoquinoline could be isolated. Rt=1.26 min (Method #TOP). Detected mass: 216.0/218.0 (M+H+).
Workup
- temperaturethe temperature was increased to 80° C
- temperaturethe mixture was cooled to room temperature
- additionpoured on ice
- filtrationThe precipitate was filtered off
- washwashed three times with dichloromethane
- customAfter drying the organic filtrates
- customwith MgSO4 and evaporation of the solvent 1.09 g of the desired isoquinoline
- customcould be isolated
Sources & evidence
- ORD record
- ord-bf36655af2a147dd95d41f26666faadc
- Source dataset
- uspto-grants-2013_08
- Patent number
- US08501736B2
Reaction notes
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