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

HRID 2045710Notes

Reaction equation

HRID 2045710 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 acidHCID 187885483-Bromo-7-methoxyquinoline

Product 1

HCID 592871093-Bromo-7-methoxyquinoline 1-oxide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

in CPBA (2.9 g, 16.8 mmol) was added to a solution of 3-bromo-7-methoxyquinoline (2.0 g, 8.40 mmol) in DCM (42 mL) at RT, and the reaction mixture was stirred at RT for 1 h. A second portion of mCPBA (2.9 g, 16.8 mmol) was then added, and the reaction mixture was stirred at RT for 18 h. 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 h
  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-18ff8156fc5b47b5bec01ec958b4a36a
Source dataset
uspto-grants-2013_11
Patent number
US08591878B2

Reaction notes

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