m-Chloroperbenzoic acid → 7-(Methoxycarbonyl)quinoline 1-oxide

HRID 509343

Reaction equation

HRID 509343 reaction equation
[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([C:11]([O:13][CH3:14])=[O:12])[CH:9]=2)[CH:4]=[CH:3][CH:2]=1.ClC1C=C(C=CC=1)C(OO)=[O:20]>C(Cl)Cl.C([O-])(O)=O.[Na+]>[CH3:14][O:13][C:11]([C:8]1[CH:9]=[C:10]2[C:5]([CH:4]=[CH:3][CH:2]=[N+:1]2[O-:20])=[CH:6][CH:7]=1)=[O:12]

Participants

5

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 12554532Methyl quinoline-7-carboxylate

Product 1

HCID 674916957-(Methoxycarbonyl)quinoline 1-oxide

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 516892Sodium BicarbonateSolvent

Procedure

To a solution of the methyl quinoline-7-carboxylate from above in DCM (10 mL) was added 3-chlorobenzoperoxoic acid (1.991 g, 11.54 mmol). The reaction was stirred for 21 h at rt. The mixture was then diluted with saturated aqueous NaHCO3 (40 mL) and the mixture was extracted with DCM (2×30 mL). The organic layers were combined, washed with saturated aqueous NaCl (40 mL), dried (MgSO4), and concentrated. The N-oxide was isolated as an orange solid which was used without purification in the next step.

Workup

  1. extractionthe mixture was extracted with DCM (2×30 mL)
  2. washwashed with saturated aqueous NaCl (40 mL)
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-7b5b119c9f4b4ca791bee28222fbc5b8
Source dataset
uspto-grants-2015_08
Patent number
US09096527B2

Linked notes

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