Methanol → HCID 12876536, compound

HRID 355109Notes

Reaction equation

HRID 355109 reaction equation
[O:1]=[C:2]1[CH2:8][C:7]2[CH:9]=[CH:10][CH:11]=[N:12][C:6]=2[S:5][C:4]2[CH:13]=[CH:14][C:15]([CH2:17][C:18](N)=[O:19])=[CH:16][C:3]1=2.[OH-:21].[K+].O.CO>C(O)(=O)C>[O:1]=[C:2]1[CH2:8][C:7]2[CH:9]=[CH:10][CH:11]=[N:12][C:6]=2[S:5][C:4]2[CH:13]=[CH:14][C:15]([CH2:17][C:18]([OH:19])=[O:21])=[CH:16][C:3]1=2

Participants

6

Reactant 4

HCID 887MethanolHCID 962WaterHCID 14797Potassium HydroxideHCID 13134782HCID 13134782, compound

Product 1

HCID 12876536HCID 12876536, compoundYield 30%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture of 50 mg of (5,6-dihydro-6-oxo benzo[b]pyrido[3,2-f]thiepin-8-yl)-acetamide, 200 mg of potassium hydroxide, 2 ml of water and 15 ml of methanol was refluxed under a nitrogen atmosphere for 4 hours. After the completion of the reaction, the solvent was distilled off to obtain a residue, to which was added ice water. The mixture was acidified with acetic acid and extracted with chloroform. The extract was washed with water and dried over anhydrous sodium sulfate. The solvent was removed by distillation to obtain an oil, which was chromatographed over silica gel and eluted with chloroform/ethanol (200/1) to obtain a solid. This solid was recrystallized from ethanol to give 15 mg (yield: 30%) of (5,6-dihydro-6-oxo benzo[b]pyrido[3,2-f]thiepin-8-yl)-acetic acid as colorless needle crystals having a melting point of 212°-213.5° C.

Workup

  1. temperaturewas refluxed under a nitrogen atmosphere for 4 hours
  2. customAfter the completion of the reaction
  3. distillationthe solvent was distilled off
  4. customto obtain a residue
  5. extractionextracted with chloroform
  6. washThe extract was washed with water
  7. dry with materialdried over anhydrous sodium sulfate
  8. customThe solvent was removed by distillation
  9. customto obtain an oil, which
  10. customwas chromatographed over silica gel
  11. washeluted with chloroform/ethanol (200/1)
  12. customto obtain a solid
  13. customThis solid was recrystallized from ethanol

Sources & evidence

ORD record
ord-2ff71552499b4e92a119c8a6b9d3684d
Source dataset
uspto-grants-1983_03
Patent number
US04377702

Reaction notes

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