Sodium Bicarbonate → HCID 178527458, compound

HRID 1005704Notes

Reaction equation

HRID 1005704 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH:11][C:12]2[CH:13]=[C:14]3[C:19](=[CH:20][CH:21]=2)[CH:18]=[N+:17]([O-])[CH:16]=[CH:15]3)(=[O:10])=[O:9])=[CH:4][CH:3]=1.C(=O)(O)[O-:24].[Na+]>C(OC(=O)C)(=O)C>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH:11][C:12]2[CH:13]=[C:14]3[C:19](=[CH:20][CH:21]=2)[C:18]([OH:24])=[N:17][CH:16]=[CH:15]3)(=[O:10])=[O:9])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 516892Sodium BicarbonateHCID 178527457HCID 178527457, compound

Product 1

HCID 178527458HCID 178527458, compound

Reagents, catalysts & solvents 1

HCID 7918Acetic AnhydrideSolvent

Conditions

Temperature
80 °C

Procedure

In acetic anhydride (0.75 ml) was dissolved 50 mg of 6-(4-chlorobenzenesulfonylamino)isoquinoline-N-oxide (intermediate in Example 83), followed by heated under stirring at 80° C. for 16 hours and then for 2 hours. After standing to cool, an aqueous saturated sodium bicarbonate was added thereto and the mixture was extracted with ethyl acetate. The extract was washed with brine, dried over anhydrous magnesium sulfate and the solvent was evaporated. The residue was dissolved in ethanol (2.0 ml) and water (0.5 ml), followed by heating under reflux for 0.5 hour. After evaporating the solvent, the residue was purified by silica gel column, to give the title compound (20 mg) as a pale red solid.

Workup

  1. temperatureby heated
  2. waitfor 2 hours
  3. temperatureto cool
  4. extractionthe mixture was extracted with ethyl acetate
  5. washThe extract was washed with brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. customthe solvent was evaporated
  8. dissolutionThe residue was dissolved in ethanol (2.0 ml)
  9. temperatureby heating
  10. temperatureunder reflux for 0.5 hour
  11. customAfter evaporating the solvent
  12. customthe residue was purified by silica gel column

Sources & evidence

ORD record
ord-307b40819c0443dfa6c27ee07385625d
Source dataset
uspto-grants-2004_09
Patent number
US06787534B2

Reaction notes

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