m-Chloroperbenzoic acid → HCID 68816493, compound

HRID 657079Notes

Reaction equation

HRID 657079 reaction equation
[F:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][C:8](=[O:12])[NH:9]2)=[N:4][CH:3]=1.ClC1C=C(C=CC=1)C(OO)=[O:18]>C(Cl)(Cl)Cl.C(Cl)Cl>[F:1][C:2]1[CH:3]=[N+:4]([O-:18])[C:5]2[CH:6]=[CH:7][C:8](=[O:12])[NH:9][C:10]=2[CH:11]=1

Participants

5

Reactant 2

HCID 70297m-Chloroperbenzoic acid3×HCID 469008017-Fluoro-1,5-naphthyridin-2(1H)-one

Product 1

HCID 68816493HCID 68816493, compound

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 6344DichloromethaneSolvent

Procedure

7-Fluoro-1,5-naphthyridin-2(1H)-one (1.280 g, 7.798 mmol) and m-chloroperoxybenzoic acid (2.123 g, ca. 1.2 eq. based on an mCPBA content of 75%) were stirred in chloroform (60 mL) at reflux overnight. Further mCPBA (0.420 g) was added and the mixture was stirred at reflux for an additional 6 hours. The mixture was diluted with DCM to a total volume of ca. 100 ml and filtered with suction. The solid collected was washed with DCM (2×20 mL) and air-dried to give 7-fluoro-1,5-naphthyridin-2(1H)-one 5-oxide as a tan solid (1.045 g, contaminated with ca. 12% starting material).

Workup

  1. temperatureat reflux overnight
  2. temperatureat reflux for an additional 6 hours
  3. filtrationfiltered with suction
  4. customThe solid collected
  5. washwas washed with DCM (2×20 mL)
  6. customair-dried

Sources & evidence

ORD record
ord-de508c97d10042b087ae40ab43b007e9
Source dataset
uspto-grants-2011_12
Patent number
US08071592B2

Reaction notes

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