m-Chloroperbenzoic acid → 4-Chloro-7-methoxy-8-methylquinoline N-oxide

HRID 579619Notes

Reaction equation

HRID 579619 reaction equation
ClC1C=CC=C(C(OO)=[O:9])C=1.[Cl:12][C:13]1[C:22]2[C:17](=[C:18]([CH3:25])[C:19]([O:23][CH3:24])=[CH:20][CH:21]=2)[N:16]=[CH:15][CH:14]=1>C(Cl)(Cl)Cl>[Cl:12][C:13]1[C:22]2[C:17](=[C:18]([CH3:25])[C:19]([O:23][CH3:24])=[CH:20][CH:21]=2)[N+:16]([O-:9])=[CH:15][CH:14]=1

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 211019544-Chloro-7-methoxy-8-methylquinoline

Product 1

HCID 576079424-Chloro-7-methoxy-8-methylquinoline N-oxideYield 18.3%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

Metachloroperbenzoic acid (90.2 g, 366.0 mmol) was added portion wise over 3 h to a solution of 4-chloro-7-methoxy-8-methylquinoline (60, 15.2 g, 73.2 mmol) in CHCl3 (1 L). Then, the solution was partitioned between ice-cooled NaOH 1N and CH2Cl2 (8 successive extractions). The organic layers were combined, dried (Na2SO4) and evaporated. The residue was purified by column chromatography (gradient of AcOEt/CH2Cl2, 1:2 to 1:0) to give 3.0 g (18.3%) of the title product 61 as a pale yellow powder: m/z=224 (M+H)+.

Workup

  1. customThen, the solution was partitioned between ice-
  2. temperaturecooled NaOH 1N and CH2Cl2 (8 successive extractions)
  3. dry with materialdried (Na2SO4)
  4. customevaporated
  5. customThe residue was purified by column chromatography (gradient of AcOEt/CH2Cl2, 1:2 to 1:0)

Sources & evidence

ORD record
ord-b9c50c5f62314a5bb0b90e503fbcf333
Source dataset
uspto-grants-2015_05
Patent number
US09040562B2

Reaction notes

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