Acetone → 3-bromoquinoline 1-oxide

HRID 1492110Notes

Reaction equation

HRID 1492110 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.CC(OO)=[O:14].CC(C)=O.C([O-])(O)=O.[Na+]>C(Cl)(Cl)Cl>[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

6

Reactant 4

HCID 180AcetoneHCID 6585Peracetic AcidHCID 214133-BromoquinolineHCID 516892Sodium Bicarbonate

Product 1

HCID 8180763-bromoquinoline 1-oxideYield 100.9%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a solution of 3-Bromoquinoline 5 (2.08 g, 10 mmol) in CHCl3 (5 ml) was added CH3CO2OH (5 ml, 32% solution in dilute HOAc, 20 mmol) and the mixture was stirred overnight. Acetone (3 ml) was added and the mixture was stirred an additional 15 min then poured into saturated NaHCO3 (aq) and extracted with CH2Cl2. The combined extracts were dried (K2CO3) and concentrated to yield pure 6 (2.26 g, 100%) as a tan solid. 1H NMR d (d=delta) (ppm): 7.7 dd (CH atom), 7.8 m (2 CH atom), 7.9 s (CH atom), 8.6 s (CH atom), 8.7 d (CH atom).

Workup

  1. stirringthe mixture was stirred an additional 15 min
  2. extractionextracted with CH2Cl2
  3. dry with materialThe combined extracts were dried (K2CO3)
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-d050b458a34e451b9cf159387ad35a4e
Source dataset
uspto-grants-1994_12
Patent number
US05372813

Reaction notes

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