Hydrogen Peroxide → HCID 18994600, compound

HRID 375258Notes

Reaction equation

HRID 375258 reaction equation
[I-].[K+].[CH3:3][N:4]([CH3:25])[C:5]([CH:7]1[CH2:16][N:15]([CH3:17])[C:14]2[N:13]=[C:12]3[CH:18]=[C:19]([F:23])[C:20]([F:22])=[CH:21][C:11]3=[CH:10][C:9]=2[C:8]1=[O:24])=[O:6].OO.S([O-])([O-])(=O)=S.[Na+].[Na+]>O.C(O)C>[CH3:3][N:4]([CH3:25])[C:5]([C:7]1[C:8](=[O:24])[C:9]2[CH:10]=[C:11]3[CH:21]=[C:20]([F:22])[C:19]([F:23])=[CH:18][C:12]3=[N:13][C:14]=2[N:15]([CH3:17])[CH:16]=1)=[O:6]

Participants

7

Reactant 4

HCID 784Hydrogen PeroxideHCID 4875Potassium IodideHCID 24477Sodium ThiosulfateHCID 18994601HCID 18994601, compound

Product 1

HCID 18994600HCID 18994600, compoundYield 78.5%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Conditions

Temperature
77 °C

Procedure

A solution of 1.35 g of potassium iodide in 10 cm3 of water is added with stirring at approximately 20° C. to a suspension of 25 g of N,N-dimethyl-7,8-difluoro-1-methyl-4-oxo-1,2,3,4-tetrahydrobenzo[b][1,8]naphthyridine-3-carboxamide in 1,000 cm3 of ethanol. The suspension is heated to 77° C., and 25 cm3 of 33% by weight hydrogen peroxide are introduced in the course of 20 minutes at this temperature. The reaction mixture is kept refluxing for a further 1 hour 30 minutes and is then cooled to approximately 20° C. 30 cm3 of 1N sodium thiosulphate solution are introduced in the course of 5 minutes at this temperature. The precipitate obtained is drained at approximately 20° C. and washed with twice 60 cm3 off water. The wet product obtained is dried under reduced pressure (20 kPa) at approximately 50° C. 19.5 g of N,N-dimethyl-7,8-difluoro-1-methyl-4-oxo-1,4-dihydrobenzo[b][1,8]naphthyridine-3-carboxamide are isolated in the form of a light yellow solid, melting point 324° C.

Workup

  1. temperatureThe reaction mixture is kept refluxing for a further 1 hour 30 minutes
  2. temperatureis then cooled to approximately 20° C
  3. customThe precipitate obtained
  4. customis drained at approximately 20° C.
  5. washwashed with twice 60 cm3 off water
  6. customThe wet product obtained
  7. customis dried under reduced pressure (20 kPa) at approximately 50° C

Sources & evidence

ORD record
ord-21e7138ec81042a5a214accaf34bba9c
Source dataset
uspto-grants-1996_01
Patent number
US05484921

Reaction notes

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