m-Chloroperbenzoic acid → HCID 66746150, compound

HRID 2047890Notes

Reaction equation

HRID 2047890 reaction equation
[C:1]([N:4]([C:8]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][C:16]=2[O:18][CH:19]2[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]2)[N:11]=[C:10]([CH3:25])[C:9]=1[C:26]([O:28][CH2:29][CH3:30])=[O:27])[C:5](=[O:7])[CH3:6])(=[O:3])[CH3:2].C1C=C(Cl)C=C(C(OO)=[O:39])C=1>ClCCCl>[C:1]([N:4]([C:8]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][C:16]=2[O:18][CH:19]2[CH2:20][CH2:21][CH2:22][CH2:23][CH2:24]2)[N+:11]([O-:39])=[C:10]([CH3:25])[C:9]=1[C:26]([O:28][CH2:29][CH3:30])=[O:27])[C:5](=[O:7])[CH3:6])(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 66746730HCID 66746730, compound

Product 1

HCID 66746150HCID 66746150, compoundYield 97.2%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

To a solution of ethyl 4-(N-acetylacetamido)-5-(cyclohexyloxy)-2-methylquinoline-3-carboxylate (Example 132b, 100 mg, 0.24 mmol) in DCE (5 mL) was added mCPBA (163 mg, 0.73 mmol). The reaction mixture was stirred at room temperature overnight under N2. The solvent was removed under reduce pressure, and the residue was purified by chromatography on silica gel eluting with 0-100% EtOAc/Hexanes gradient to give the title compound as an orange oil (100 mg, 97%). MS 429 (MH+).

Workup

  1. customThe solvent was removed
  2. customthe residue was purified by chromatography on silica gel eluting with 0-100% EtOAc/Hexanes gradient

Sources & evidence

ORD record
ord-a679b3836eb54943b4dbb115e702d35a
Source dataset
uspto-grants-2013_11
Patent number
US08592592B2

Reaction notes

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