5-Bromoisoquinoline → Isoquinoline, 5-bromo-, 2-oxide

HRID 875043Notes

Reaction equation

HRID 875043 reaction equation
[Br:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][N:6]=[CH:7]2.O.O.O.O.O.O.C(O[O-])(=O)C1C(=CC=CC=1)C([O-])=[O:22].[Mg+2]>CC(O)C>[Br:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][N+:6]([O-:22])=[CH:7]2

Participants

4

Reactant 2

HCID 7364875-BromoisoquinolineHCID 21894687Magnesium 2-(dioxidan-2-ide-1-carbonyl)benzoate--water (1/1/6)

Product 1

HCID 22665708Isoquinoline, 5-bromo-, 2-oxide

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

3.1 A suspension of 6.24 g (30.0 mmol) of 5-bromoisoquinoline and 17.5 g (30 mmol) of magnesium monoperoxyphthalate hexahydrate (85%) in 120 ml of 2-propanol is stirred at room temperature for 50 hours. The reaction mixture is evaporated in vacuo, and saturated sodium chloride solution, saturated sodium hydrogencarbonate solution and dichloromethane are added. The organic phase is separated off and washed a number of times with saturated sodium chloride solution. The organic phase is dried over sodium sulfate and evaporated. The residue is stirred with tert-butyl methyl ether, giving 5-bromoisoquinoline 2-oxide as colourless crystals; HPLC/MS: 1.51 min, [M+H] 224/226.

Workup

  1. customThe reaction mixture is evaporated in vacuo, and saturated sodium chloride solution, saturated sodium hydrogencarbonate solution and dichloromethane
  2. additionare added
  3. customThe organic phase is separated off
  4. washwashed a number of times with saturated sodium chloride solution
  5. dry with materialThe organic phase is dried over sodium sulfate
  6. customevaporated
  7. stirringThe residue is stirred with tert-butyl methyl ether

Sources & evidence

ORD record
ord-16498351d1074d418446eca756809d60
Source dataset
uspto-grants-2015_03
Patent number
US08981101B2

Reaction notes

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