m-Chloroperbenzoic acid → HCID 57815209, compound

HRID 1256182Notes

Reaction equation

HRID 1256182 reaction equation
[Br:1][C:2]1[CH:3]=[N:4][C:5]2[C:10]([CH:11]=1)=[N:9][CH:8]=[CH:7][CH:6]=2.ClC1C=CC=C(C(OO)=[O:20])C=1>C(Cl)Cl>[Br:1][C:2]1[CH:3]=[N:4][C:5]2[CH:6]=[CH:7][CH:8]=[N+:9]([O-:20])[C:10]=2[CH:11]=1.[Br:1][C:2]1[CH:3]=[N+:4]([O-:20])[C:5]2[C:10]([CH:11]=1)=[N:9][CH:8]=[CH:7][CH:6]=2

Participants

5

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 128788183-Bromo-1,5-naphthyridine

Product 2

HCID 57815209HCID 57815209, compoundHCID 58310524HCID 58310524, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

4.43 g (21.2 mmol, 1 eq) of 3-bromo-1,5-naphthyridine (W. Czuba, Recueil des Travaux Chimiques des Pays-Bas 1963, 82, 988-996) were introduced in 165 mL of methylene chloride. 5.23 g (21.2 mmol, 1 eq) of meta-chloroperbenzoic acid were then added portionwise at 0° C. The mixture was stirred at rt for 18 h. The mixture was washed with 1M aqueous NaOH solution and water. Organic layer was dried over Na2SO4, filtered and evaporated to dryness. The residue was purified by column chromatography using methylene chloride and then methylene chloride/ethanol: 98/2 as eluent. The solvent was evaporated to dryness to afford 3.08 g of 3-bromo-1,5-naphthyridine-5-oxide (pale yellow powder) with 64% yield and 1.00 g of 3-bromo-1,5-naphthyridine-1-oxide (yellow powder) with 21% yield.

Workup

  1. washThe mixture was washed with 1M aqueous NaOH solution and water
  2. dry with materialOrganic layer was dried over Na2SO4
  3. filtrationfiltered
  4. customevaporated to dryness
  5. customThe residue was purified by column chromatography
  6. customThe solvent was evaporated to dryness

Sources & evidence

ORD record
ord-157d1c9e7e6e45b4b3e95202712b7e8c
Source dataset
uspto-grants-2013_06
Patent number
US08461178B2

Reaction notes

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