Sodium Hydroxide → HCID 21998681, compound

HRID 1976568Notes

Reaction equation

HRID 1976568 reaction equation
[CH:1]12[CH2:7][CH2:6][CH:5]1[CH2:4][C:3](=[O:8])[CH2:2]2.[NH2:9]OS(O)(=O)=O.[OH-].[Na+]>C(O)=O>[O:8]=[C:3]1[CH2:4][CH:5]2[CH:1]([CH2:7][CH2:6]2)[CH2:2][NH:9]1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 76284hydroxylamine-O-sulfonic acidHCID 1255042263492-36-4

Product 1

HCID 21998681HCID 21998681, compoundYield 8.8%

Reagents, catalysts & solvents 1

HCID 284Formic AcidSolvent

Procedure

To a solution of 0.48 g of bicyclo[3.2.0]heptan-3-one in 8 ml of formic acid was added 725 mg of hydroxylamine-O-sulfonic acid, followed by heat-refluxing for 3 hours. The reaction mixture was allowed to cool, poured into ice water, neutralized with a 5N sodium hydroxide aqueous solution, and extracted with chloroform. The organic layer was washed, dried, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography to give 48 mg of the title compound as a brown solid, which had the following physical properties.

Workup

  1. temperatureby heat-refluxing for 3 hours
  2. temperatureto cool
  3. extractionextracted with chloroform
  4. washThe organic layer was washed
  5. customdried
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-cc2267c4ffdb46388136ebe23dc4c561
Source dataset
uspto-grants-2001_05
Patent number
US06228866B1

Reaction notes

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