m-Chloroperbenzoic acid → HCID 86732726, compound

HRID 525860Notes

Reaction equation

HRID 525860 reaction equation
C([C:4]1[C:13](=[O:14])[C:12]2[C:7](=[CH:8][CH:9]=[C:10]([C:15]([O:17][CH2:18][CH3:19])=[O:16])[CH:11]=2)[N:6]([CH3:20])[CH:5]=1)(=O)C.ClC1C=CC=C(C(OO)=[O:29])C=1>ClCCl>[OH:29][C:4]1[C:13](=[O:14])[C:12]2[C:7](=[CH:8][CH:9]=[C:10]([C:15]([O:17][CH2:18][CH3:19])=[O:16])[CH:11]=2)[N:6]([CH3:20])[CH:5]=1

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 86732725HCID 86732725, compound

Product 1

HCID 86732726HCID 86732726, compoundYield 61.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of ethyl 3-acetyl-1-methyl-4-oxo-1,4-dihydroquinoline-6-carboxylate (1.79 g, 6.55 mmol) in dichloromethane (40 ml) was added meta-chloroperbenzoic acid (2.2057 g, 9.84 mmol). The mixture was stirred at room temperature for 1 h, then concentrated under reduced pressure to roughly one half of the reaction volume. The resulting precipitate (O-acetate) was collected, added to methanol (20.0 ml), and heated at 65° C. overnight. After cooling, the reaction was filtered, and the precipitate was washed with dichloromethane to give ethyl 3-hydroxy-1-methyl-4-oxo-1,4-dihydroquinoline-6-carboxylate (0.9956 g, 4.03 mmol, 61.5% yield) as white solid. LCMS: (M+H)+: 248.0.

Workup

  1. concentrationconcentrated under reduced pressure to roughly one half of the reaction volume
  2. customThe resulting precipitate (O-acetate) was collected
  3. additionadded to methanol (20.0 ml)
  4. temperatureheated at 65° C. overnight
  5. temperatureAfter cooling
  6. filtrationthe reaction was filtered
  7. washthe precipitate was washed with dichloromethane

Sources & evidence

ORD record
ord-6bbc0f93076245e9bd0ed210b837a543
Source dataset
uspto-grants-2016_05
Patent number
US09340556B2

Reaction notes

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