m-Chloroperbenzoic acid → 7-Chloro-6-fluoro-isoquinoline 2-oxide
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].ClC1C=CC=C(C(OO)=[O:21])C=1>ClCCl>[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][N+:8]([O-:21])=[CH:9]2)=[CH:4][C:3]=1[F:12]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 5 °C
Procedure
50 g of 7-chloro-6-fluoro-isoquinoline (prepared according to WO 2007/012422) were dissolved in dichloromethane and cooled to 5° C. 69.6 g of m-chloro-perbenzoic acid (70%) were added portionwise. The mixture was stirred at room temperature. When conversion was complete, the mixture was diluted with 1.5 L of dichloromethane and washed three times with saturated sodium bicarbonate solution. The organic layer was dried over sodium sulphate and evaporated to dryness to give 47.6 g of the desired product 9. Rt=0.98 min (Method 5). Detected mass: 198.1 (M+H+).
Workup
- washwashed three times with saturated sodium bicarbonate solution
- dry with materialThe organic layer was dried over sodium sulphate
- customevaporated to dryness
Sources & evidence
- ORD record
- ord-f92e365d60f84545a922f08124f7a690
- Source dataset
- uspto-grants-2013_09
- Patent number
- US08541449B2
Reaction notes
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