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

HRID 1621289Notes

Reaction equation

HRID 1621289 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=C(C=CC=1)C(OO)=[O:18]>ClCCl>[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][N+:8]([O-:18])=[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 (56) were in dissolved in 500 ml of dichloromethane. At room temperature 50.9 g (206.5 mmol) of 3-chloro-peroxy benzoic acid (70%) were added and the mixture was stirred at room temperature until complete conversion was achieved. For workup, the precipitate was filtered off and washed with dichloromethane. The filtrate was washed twice with NaHCO3-solution. The layers were separated and the aqueous phase was extracted twice with dichloromethane. The organic phases were dried with MgSO4 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 NaHCO3-solution
  4. customThe layers were separated
  5. extractionthe aqueous phase was extracted twice with dichloromethane
  6. dry with materialThe organic phases were dried with MgSO4
  7. customevaporated

Sources & evidence

ORD record
ord-416b6fdfb27740bd9c980b3b9f299cc6
Source dataset
uspto-grants-2014_07
Patent number
US08772492B2

Reaction notes

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