Sodium Sulfite → 3-Bromo-7-methoxyquinoline 1-oxide

HRID 389209Notes

Reaction equation

HRID 389209 reaction equation
[Br:1][C:2]1[CH:3]=[N:4][C:5]2[C:10]([CH:11]=1)=[CH:9][CH:8]=[C:7]([O:12][CH3:13])[CH:6]=2.C1C=C(Cl)C=C(C(OO)=[O:22])C=1.[O-]S([O-])=O.[Na+].[Na+]>C(Cl)Cl>[Br:1][C:2]1[CH:3]=[N+:4]([O-:22])[C:5]2[C:10]([CH:11]=1)=[CH:9][CH:8]=[C:7]([O:12][CH3:13])[CH:6]=2

Participants

5

Reactant 3

HCID 24437Sodium SulfiteHCID 70297m-Chloroperbenzoic acid2×HCID 187885483-Bromo-7-methoxyquinoline

Product 1

HCID 592871093-Bromo-7-methoxyquinoline 1-oxide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 3-bromo-7-methoxyquinoline (2.0 g, 8.40 mmol) in DCM (42 mL) at RT, mCPBA (2.9 g, 16.8 mmol) was added, and the reaction mixture was stirred at RT for 1 hour. A second portion of mCPBA (2.9 g, 16.8 mmol) was then added, and the reaction mixture was stirred at RT for 18 hours. The reaction mixture was poured onto 10% aqueous Na2SO3 and DCM, and the layers were separated. The organic layer was washed with NaHCO3, dried over MgSO4, filtered and concentrated. The resulting product was used with no further purification. LRMS (M+H)+=254.2.

Workup

  1. stirringthe reaction mixture was stirred at RT for 18 hours
  2. customthe layers were separated
  3. washThe organic layer was washed with NaHCO3
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe resulting product was used with no further purification

Sources & evidence

ORD record
ord-3371af0cd50e4fcca73a4b259f3af49e
Source dataset
uspto-grants-2013_02
Patent number
US08377874B2

Reaction notes

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