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m-Chloroperbenzoic acid → 4-methoxy-6-(4-methoxybenzyl)-N,N-dimethyl-5-oxo-5,6,7,8-tetrahydro-2,6-naphthyridine-1-carboxamide 2-oxide

HRID 1817345
Notes
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Reaction equation

HRID 1817345 reaction equation
[CH3:1][O:2][C:3]1[C:12]2[C:11](=[O:13])[N:10]([CH2:14][C:15]3[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[CH:17][CH:16]=3)[CH2:9][CH2:8][C:7]=2[C:6]([C:23]([N:25]([CH3:27])[CH3:26])=[O:24])=[N:5][CH:4]=1.C1C=C(Cl)C=C(C(OO)=[O:36])C=1>C(Cl)Cl>[CH3:1][O:2][C:3]1[CH:4]=[N+:5]([O-:36])[C:6]([C:23]([N:25]([CH3:27])[CH3:26])=[O:24])=[C:7]2[C:12]=1[C:11](=[O:13])[N:10]([CH2:14][C:15]1[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[CH:17][CH:16]=1)[CH2:9][CH2:8]2
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 690697114-methoxy-6-(4-methoxybenzyl)-N,N-dimethyl-5-oxo-5,6,7,8-tetrahydro-2,6-naphthyridine-1-carboxamide

Product 1

HCID 690604854-methoxy-6-(4-methoxybenzyl)-N,N-dimethyl-5-oxo-5,6,7,8-tetrahydro-2,6-naphthyridine-1-carboxamide 2-oxide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A 100 ml CH2Cl2 solution of 12 g 4-methoxy-6-(4-methoxybenzyl)-N,N-dimethyl-5-oxo-5,6,7,8-tetrahydro-2,6-naphthyridine-1-carboxamide and 16.8 g mCPBA (maximum 77% purity) was allowed to stir at room temperature until the starting material was consumed (5 hours). The reaction was washed four times with 100 mL sat aqueous NaHCO3 then the organic layer was concentrated. The crude reaction was dissolved in 250 mL CH2Cl2 and the excess mCPBA was then quenched by vigorous stirring with a sat aq sodium sulfite solution for 30 minutes (both organic and aqueous layers were cloudy initially but then turned transparent). The layers were separated and the organic washed twice with sat aqueous NaHCO3. The organic layer was dried over sodium sulfate and concentrated to pure product by HPLC/MS and NMR.

Workup

  1. customwas consumed (5 hours)
  2. washThe reaction was washed four times with 100 mL
  3. concentrationthe organic layer was concentrated
  4. customThe crude reaction
  5. customthe excess mCPBA was then quenched
  6. stirringby vigorous stirring with a sat aq sodium sulfite solution for 30 minutes (both organic and aqueous layers
  7. customThe layers were separated
  8. washthe organic washed twice with sat aqueous NaHCO3
  9. dry with materialThe organic layer was dried over sodium sulfate
  10. concentrationconcentrated to pure product by HPLC/MS and NMR

Sources & evidence

ORD record
ord-7a77e3fa173241daaa03b9622fb86785
Source dataset
uspto-grants-2009_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07598264B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes