Hydrochloric Acid → HCID 53729196, compound

HRID 1439819Notes

Reaction equation

HRID 1439819 reaction equation
[CH2:1]([C:5]1[CH:6]=[CH:7][C:8]2[S:18][CH2:17][C:16]3[C:15](=[O:19])[CH:14]=[C:13]([C:20]([OH:22])=[O:21])[NH:12][C:11]=3[C:9]=2[CH:10]=1)[CH2:2][CH2:3][CH3:4].Cl.[CH3:24]O>>[CH3:24][O:21][C:20]([C:13]1[NH:12][C:11]2[C:9]3[CH:10]=[C:5]([CH2:1][CH2:2][CH2:3][CH3:4])[CH:6]=[CH:7][C:8]=3[S:18][CH2:17][C:16]=2[C:15](=[O:19])[CH:14]=1)=[O:22]

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 887MethanolHCID 12677804HCID 12677804, compound

Product 1

HCID 53729196HCID 53729196, compound

Procedure

A solution of 9-butyl-1,4-dihydro-4-oxo-5H-[1]benzothiopyrano-[4,3-b]pyridine-2-carboxylic acid (1.82 g, described in Example 84) in 350 ml of anhydrous methanol saturated with hydrogen chloride is heated at reflux for 17 hours. The solvent is removed by evaporation. Water is added to the residue and the aqueous mixture is extracted with chloroform. The organic extract is dried over magnesium sulfate and evaporated. The residue is subjected to chromatography on silica gel using benzene-ethyl acetate (4:1) as eluant. The eluate is evaporated and the residue is crystallized from ether to give the title compound, m.p. 144°-146° C.

Workup

  1. temperatureat reflux for 17 hours
  2. customThe solvent is removed by evaporation
  3. additionWater is added to the residue
  4. extractionthe aqueous mixture is extracted with chloroform
  5. extractionThe organic extract
  6. dry with materialis dried over magnesium sulfate
  7. customevaporated
  8. customThe eluate is evaporated
  9. customthe residue is crystallized from ether

Sources & evidence

ORD record
ord-8c928f470cfe4aaa90107e7858dbcbbc
Source dataset
uspto-grants-1977_11
Patent number
US04060619

Reaction notes

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