Iodine → HCID 13336760, compound

HRID 1462912Notes

Reaction equation

HRID 1462912 reaction equation
[SH:1][CH2:2][C:3]([N:5]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[CH2:8][CH2:7][CH:6]1[C:15]([OH:17])=[O:16])=[O:4].[OH-:18].[Na+].II>O.C(O)C>[O:18]=[C:3]([N:5]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[CH2:8][CH2:7][CH:6]1[C:15]([OH:17])=[O:16])[CH2:2][S:1][S:1][CH2:2][C:3]([N:5]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[CH2:8][CH2:7][CH:6]1[C:15]([OH:17])=[O:16])=[O:4]

Participants

6

Reactant 3

HCID 807Iodine2×HCID 14798Sodium Hydroxide2×HCID 13336759HCID 13336759, compound

Product 1

HCID 13336760HCID 13336760, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

(±)-1,2,3,4-Tetrahydro-1-(2-mercapto-1-oxoethyl)-2-quinolinecarboxylic acid (3 g) was suspended in water (40 ml) and the pH was adjusted to 6.5 with 2 N sodium hydroxide. A saturated solution of iodine in ethanol was then added dropwise while maintaining the pH at 6.5 by the slow addition of 2 N sodium hydroxide. When a yellow color remained for at least five minutes, addition of the iodine solution was terminated and the yellow color was discharged with saturated aqueous sodium thiosulfate. The mixture was then acidified with concentrated hydrochloric acid and extracted with ethyl acetate. The combined extracts were washed with 10% hydrochloric acid and water, dried over magnesium sulfate, and concentrated under reduced pressure. The (±) 1,1'-[dithiobis(1-oxo-2,1-ethanediyl)]-bis-1,2,3,4-tetrahydro-2-quinolinecarboxylic acid was recrystallized from ethyl acetate; yield 0.7 g, m.p. 172°-174°.

Workup

  1. temperaturewhile maintaining the pH at 6.5
  2. waitWhen a yellow color remained for at least five minutes
  3. customwas terminated
  4. extractionextracted with ethyl acetate
  5. washThe combined extracts were washed with 10% hydrochloric acid and water
  6. dry with materialdried over magnesium sulfate
  7. concentrationconcentrated under reduced pressure
  8. customThe (±) 1,1'-[dithiobis(1-oxo-2,1-ethanediyl)]-bis-1,2,3,4-tetrahydro-2-quinolinecarboxylic acid was recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-e3d75ce663704b88b26efb59836cc8c4
Source dataset
uspto-grants-1984_07
Patent number
US04461896

Reaction notes

Loading…