Potassium Carbonate → HCID 54340306, compound

HRID 618725Notes

Reaction equation

HRID 618725 reaction equation
[F:1][C:2]1[C:3]([F:13])=[CH:4][C:5]2[O:9][C:8]([C:10]#[N:11])=[CH:7][C:6]=2[CH:12]=1.Cl.[NH2:15][OH:16].C(=O)([O-])[O-].[K+].[K+]>C(O)C>[F:1][C:2]1[C:3]([F:13])=[CH:4][C:5]2[O:9][C:8]([C:10](=[N:15][OH:16])[NH2:11])=[CH:7][C:6]=2[CH:12]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 443297Hydroxyamine hydrochlorideHCID 218483295,6-Difluoro-2-benzofurancarbonitrile

Product 1

HCID 54340306HCID 54340306, compoundYield 61.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 1.2 g (6.7 mmol) of 5,6-difluorobenzofuran-2-carbonitrile, 0.93 g (13.4 mmol) of hydroxylamine hydrochloride, 2.78 g (20.1 mmol) of potassium carbonate and 50 ml of anhydrous ethanol was heated under reflux over 16 hours while stirring. Subsequently, the solid was filtered off and the filtrate was concentrated in a vacuum. The crude product obtained was purified by column chromatography on silica gel (ethyl acetate/hexane 3:2). There was obtained 0.88 g (61%) of 5,6-difluorobenzofuran-2-carboxamidoxime as a light yellow solid with m.p. 184°.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux over 16 hours
  3. filtrationSubsequently, the solid was filtered off
  4. concentrationthe filtrate was concentrated in a vacuum
  5. customThe crude product obtained
  6. customwas purified by column chromatography on silica gel (ethyl acetate/hexane 3:2)

Sources & evidence

ORD record
ord-d2823137acf746baa079c71190e3f402
Source dataset
uspto-grants-1999_09
Patent number
US05955495

Reaction notes

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