6-Nitroquinoline → 6-Nitroquinoline N-oxide

HRID 751091Notes

Reaction equation

HRID 751091 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][CH:13]=1)[N:10]=[CH:9][CH:8]=[CH:7]2)([O-:3])=[O:2].C1C=C(Cl)C=C(C(OO)=[O:22])C=1>C(Cl)(Cl)Cl>[N+:1]([C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][CH:13]=1)[N+:10]([O-:22])=[CH:9][CH:8]=[CH:7]2)([O-:3])=[O:2]

Participants

4

Reactant 2

HCID 119456-NitroquinolineHCID 70297m-Chloroperbenzoic acid

Product 1

HCID 836466-Nitroquinoline N-oxideYield 93.9%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

Commercially available 6-nitroquinoline (1.0 g, 5.6 mmol) was dissolved in CHCl3 (30 mL) and mCPBA (1.76 g, 7.8 mmol) was added portionwise and the reactions stirred at rt for 48 h. The mixture was then washed with saturated aqueous NaHCO3, 1 N aqueous NaOH, and 5% aqueous NaHSO3, dried (Na2SO4), filtered and concentrated under reduced pressure to give compound 45A (1.0 g, 93%) as a light yellow solid. LC/MS m/z 191 [M+H]+. 45B. 2-Cyano-6-nitroquinoline

Workup

  1. washThe mixture was then washed with saturated aqueous NaHCO3, 1 N aqueous NaOH, and 5% aqueous NaHSO3
  2. dry with materialdried (Na2SO4)
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-efe09afebe174837b6157c6c67c21d0a
Source dataset
uspto-grants-2008_07
Patent number
US07405234B2

Reaction notes

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