Sodium Bicarbonate → HCID 178527458, compound

HRID 1173146Notes

Reaction equation

HRID 1173146 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

6-(4-Chlorobenzenesulfonylamino)isoquinoline-N-oxide (intermediate in Synthetic Example 83b, 50 mg) was dissolved in acetic acid anhydride (0.75 ml), followed by heating under stirring at 80° C. for 16 hours. Then, the mixture was refluxed under heating for 2 hours. After cooling as it was, an aqueous saturated sodium bicarbonate was added thereto, followed by extracting with ethyl acetate. The extract was washed with brine and dried over anhydrous magnesium sulfate. After evaporating the solvent, the residue was dissolved in ethanol (2.0 ml) and water (0.5 ml), followed by heating under reflux for 0.5 hours. 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 heating
  2. temperatureThen, the mixture was refluxed
  3. temperatureunder heating for 2 hours
  4. temperatureAfter cooling as it
  5. extractionby extracting with ethyl acetate
  6. washThe extract was washed with brine
  7. dry with materialdried over anhydrous magnesium sulfate
  8. customAfter evaporating the solvent
  9. dissolutionthe residue was dissolved in ethanol (2.0 ml)
  10. temperatureby heating
  11. temperatureunder reflux for 0.5 hours
  12. customAfter evaporating the solvent
  13. customthe residue was purified by silica gel column

Sources & evidence

ORD record
ord-7d3d55207d1e471e98a4093c77cd180e
Source dataset
uspto-grants-2010_11
Patent number
US07834049B2

Reaction notes

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