Methyl morpholine oxide → HCID 58297051, compound

HRID 1969437Notes

Reaction equation

HRID 1969437 reaction equation
[F:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[C:4](=[O:31])[C:5]([C:26]([O:28][CH2:29][CH3:30])=[O:27])=[CH:6][N:7]2[CH2:12][C:13]1[CH:18]=[CH:17][C:16]([N:19]2[CH:23]=[CH:22][C:21]([CH2:24][OH:25])=[N:20]2)=[CH:15][CH:14]=1.C[N+]1([O-])CCOCC1>ClCCl.[Ru]([O-])(=O)(=O)=O.C([N+](CCC)(CCC)CCC)CC>[F:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[C:4](=[O:31])[C:5]([C:26]([O:28][CH2:29][CH3:30])=[O:27])=[CH:6][N:7]2[CH2:12][C:13]1[CH:14]=[CH:15][C:16]([N:19]2[CH:23]=[CH:22][C:21]([CH:24]=[O:25])=[N:20]2)=[CH:17][CH:18]=1

Participants

5

Reactant 2

HCID 82029Methyl morpholine oxideHCID 58297057HCID 58297057, compound

Product 1

HCID 58297051HCID 58297051, compound

Reagents, catalysts & solvents 2

HCID 178419074HCID 178419074, compoundCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of ethyl 5-fluoro-1-{4-[3-(hydroxymethyl)-1H-pyrazol-1-yl]benzyl}-4-oxo-1,4-dihydroquinoline-3-carboxylate (0.300 g, 0.712 mmol) in 10 mL of dichloromethane containing crushed molecular sieves was added 4-methylmorpholine N-oxide (0.108 g, 0.925 mmol). After 10 minutes, tetrapropylammonium perruthenate (0.025 g, 0.071 mmol) was added. After an hour, the reaction mixture was filtered through celite and concentrated in vacuo. The crude material was subjected to chromatography on silica gel eluting with 0-3% MeOH in DCM to provide Ethyl 5-fluoro-1-[4-(3-formyl-1H-pyrazol-1-yl)benzyl]-4-oxo-1,4-dihydroquinoline-3-carboxylate which gave a proton NMR spectrum consistent with theory and a mass ion (ES+) of 420.1 for M+H+.

Workup

  1. waitAfter an hour
  2. filtrationthe reaction mixture was filtered through celite and
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-d9250c9d79a5485db71ad04bf6bca47d
Source dataset
uspto-grants-2013_04
Patent number
US08426598B2

Reaction notes

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