Peracetic Acid → 3-bromoquinoline 1-oxide

HRID 861008Notes

Reaction equation

HRID 861008 reaction equation
[Br:1][C:2]1[CH:3]=[N:4][C:5]2[C:10]([CH:11]=1)=[CH:9][CH:8]=[CH:7][CH:6]=2.C(OO)(=[O:14])C>C(Cl)Cl.C([O-])(O)=O.[Na+]>[Br:1][C:2]1[CH:3]=[N+:4]([O-:14])[C:5]2[C:10]([CH:11]=1)=[CH:9][CH:8]=[CH:7][CH:6]=2

Participants

5

Reactant 2

HCID 6585Peracetic AcidHCID 214133-Bromoquinoline

Product 1

HCID 8180763-bromoquinoline 1-oxide

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 516892Sodium BicarbonateSolvent

Procedure

To a solution of 3-bromo-quinoline (1.0 eq.) in CH2Cl2 (0.2M) was added peracetic acid (2.0 eq.). The mixture was stirred for 12 h, poured in saturated aqueous NaHCO3 and extracted with EtOAc (2×). The combined organic extracts were washed with brine, dried over Na2SO4, filtered and concentrated. Crystallization from CH2Cl2:Hex afforded the title compound as a white solid.

Workup

  1. extractionextracted with EtOAc (2×)
  2. washThe combined organic extracts were washed with brine
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customCrystallization from CH2Cl2

Sources & evidence

ORD record
ord-2f223ed5014143df85601febc1b818ed
Source dataset
uspto-grants-2006_12
Patent number
US07153968B2

Reaction notes

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