m-Chloroperbenzoic acid → N-[(4-chlorophenyl)methyl]-1-(3-methylsulfinylpropyl)-6-(morpholinomethyl)-4-oxo-quinoline-3-carboxamide

HRID 1068007Notes

Reaction equation

HRID 1068007 reaction equation
[Cl:1][C:2]1[CH:34]=[CH:33][C:5]([CH2:6][NH:7][C:8]([C:10]2[C:19](=[O:20])[C:18]3[C:13](=[CH:14][CH:15]=[C:16]([CH2:21][N:22]4[CH2:27][CH2:26][O:25][CH2:24][CH2:23]4)[CH:17]=3)[N:12]([CH2:28][CH2:29][CH2:30][S:31][CH3:32])[CH:11]=2)=[O:9])=[CH:4][CH:3]=1.O.C1(C)C=CC(S(O)(=O)=[O:43])=CC=1.ClC1C=C(C=CC=1)C(OO)=O>ClCCl>[Cl:1][C:2]1[CH:34]=[CH:33][C:5]([CH2:6][NH:7][C:8]([C:10]2[C:19](=[O:20])[C:18]3[C:13](=[CH:14][CH:15]=[C:16]([CH2:21][N:22]4[CH2:27][CH2:26][O:25][CH2:24][CH2:23]4)[CH:17]=3)[N:12]([CH2:28][CH2:29][CH2:30][S:31]([CH3:32])=[O:43])[CH:11]=2)=[O:9])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 70297m-Chloroperbenzoic acidHCID 521998p-Toluenesulfonic acid monohydrateHCID 16073877N-[(4-chlorophenyl)methyl]-1-(3-methylsulfanylpropyl)-6-(morpholinomethyl)-4-oxo-quinoline-3-carboxamide

Product 1

HCID 16073880N-[(4-chlorophenyl)methyl]-1-(3-methylsulfinylpropyl)-6-(morpholinomethyl)-4-oxo-quinoline-3-carboxamideYield 67.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of N-(4-chlorobenzyl)-1-[3-(methylsulfanyl)propyl]-6-(4-morpholinylmethyl)-4-oxo-1,4-dihydro-3-quinolinecarboxamide (0.10 gm) from Example No. 61 in dichloromethane (2 mL) at 0° C. is added p-toluenesulfonic acid hydrate (0.04 gm) followed by m-chloroperoxybenzoic acid (˜85%)(0.045 gm). The mixture is stirred for 0.5 hrs. The reaction mixture is diluted with dichloromethane, washed with saturated aqueous sodium sulfite, saturated aqueous sodium bicarbonate, brine, dried (Na2SO4) and concentrated under reduced pressure. The crude product is purified by flash column chromatography eluting with 3% to 9% methanol in dichloromethane. The product fractions are combined and recrystallized from ethyl acetate-methanol-hexanes to afford 0.07 gm of the title compound as a white solid.

Workup

  1. washwashed with saturated aqueous sodium sulfite, saturated aqueous sodium bicarbonate, brine
  2. dry with materialdried (Na2SO4)
  3. concentrationconcentrated under reduced pressure
  4. customThe crude product is purified by flash column chromatography
  5. washeluting with 3% to 9% methanol in dichloromethane
  6. customrecrystallized from ethyl acetate-methanol-hexanes

Sources & evidence

ORD record
ord-cfb64910d6fb443ba511e62990da20cc
Source dataset
uspto-grants-2001_06
Patent number
US06248739B1

Reaction notes

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