m-Chloroperbenzoic acid → 1-Oxo-1lambda~5~-1,5-naphthyridine

HRID 513748Notes

Reaction equation

HRID 513748 reaction equation
C1C=C(Cl)C=C(C(OO)=[O:9])C=1.[N:12]1[C:21]2[C:16](=[N:17][CH:18]=[CH:19][CH:20]=2)[CH:15]=[CH:14][CH:13]=1>C(Cl)Cl>[N+:12]1([O-:9])[C:21]2[C:16](=[N:17][CH:18]=[CH:19][CH:20]=2)[CH:15]=[CH:14][CH:13]=1

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 1360701,5-Naphthyridine

Product 1

HCID 3392321-Oxo-1lambda~5~-1,5-naphthyridineYield 84.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

m-CPBA (1.2 g, 6.91 mmol) was added in 3 portions (after every 3 h) to a solution of 1,5-naphthyridine (1.0 g, 7.68 mmol) in dry DCM (60 ml). After completion of the reaction, the mixture was concentrated in vacuo. The crude residue was purified by column chromatography with DCM/MeOH (98:2) as the eluent to get title compound (0.85 g, 76%).

Workup

  1. customAfter completion of the reaction
  2. concentrationthe mixture was concentrated in vacuo
  3. customThe crude residue was purified by column chromatography with DCM/MeOH (98:2) as the eluent

Sources & evidence

ORD record
ord-961c72abf7164039bb788d5de36401b8
Source dataset
uspto-grants-2015_08
Patent number
US09102688B2

Reaction notes

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