m-Chloroperbenzoic acid → 7-Chloro-6-fluoro-isoquinoline 2-oxide

HRID 1913110Notes

Reaction equation

HRID 1913110 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

HCID 70297m-Chloroperbenzoic acidHCID 534189227-Chloro-6-fluoroisoquinoline

Product 1

HCID 598182547-Chloro-6-fluoro-isoquinoline 2-oxideYield 67.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

25 g (137.7 mmol) of 7-chloro-6-fluoro-isoquinoline (4) were in dissolved in 500 ml of dichloromethane. At room temperature 50.9 g (206.5 mmol) of m-chloro perbenzoic acid (70%) were added and the mixture was stirred at room temperature until complete conversion is achieved. For workup, the precipitate was filtered off and washed with dichloromethane. The filtrate was washed twice with sodium bicarbonate solution. The layers were separated and the aqueous phase was extracted twice with dichloromethane. The organic phases were dried with magnesium sulfate and evaporated. The so obtained solid material (18.4 g) was used without further purification. Rt=0.87 min (Method C). Detected mass: 198.1/200.1 (M+H+).

Workup

  1. filtrationFor workup, the precipitate was filtered off
  2. washwashed with dichloromethane
  3. washThe filtrate was washed twice with sodium bicarbonate solution
  4. customThe layers were separated
  5. extractionthe aqueous phase was extracted twice with dichloromethane
  6. dry with materialThe organic phases were dried with magnesium sulfate
  7. customevaporated

Sources & evidence

ORD record
ord-0041d456ec504317a28d9168f0c0559c
Source dataset
uspto-grants-2013_12
Patent number
US08609691B2

Reaction notes

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