Hydrochloric Acid → 2-(1-Carboxy-1-methylethylthio)-3-phenylquinoline

HRID 1903239Notes

Reaction equation

HRID 1903239 reaction equation
[C:1]1([C:7]2[C:8](=[S:17])[NH:9][C:10]3[C:15]([CH:16]=2)=[CH:14][CH:13]=[CH:12][CH:11]=3)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H-].[Na+].[H][H].Br[C:23]([CH3:28])([CH3:27])[C:24]([OH:26])=[O:25].Cl>CN(C)C=O>[C:24]([C:23]([CH3:28])([S:17][C:8]1[C:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)=[CH:16][C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[N:9]=1)[CH3:27])([OH:26])=[O:25]

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 24758Sodium hydrideHCID 749242-Bromo-2-methylpropanoic acidHCID 132002063-Phenylquinolin-2-thioneHCID 178418361HCID 178418361, compound

Product 1

HCID 132003062-(1-Carboxy-1-methylethylthio)-3-phenylquinoline

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

3-Phenylquinolin-2-thione (1.18 g.) was added to a suspension of sodium hydride (0.46 g. of a 50% w/w dispersion in mineral oil) in dimethylformamide (10 ml.) at 0°-5°. When all the hydrogen had evolved, 2-bromoisobutyric acid (0.88 g.) was added and the mixture was heated at 80° for 16 hr. The mixture was cooled to ambient temperature, poured into ice-water (50 ml.), acidified to pH 2 with concentrated hydrochloric acid, and extracted with ethyl acetate (3×25 ml.). The ethyl acetate extract was washed with brine (25 ml.) and then dried (MgSO4). The solvent was evaporated and the residual oil was chromatographed on silica (100 g., Merck type 7734), eluted with increasing concentrations of ethyl acetate in petroleum ether. The eluate obtained with 10% v/v ethyl acetate in petroleum ether was evaporated and the solid residue crystallised from cyclohexane to give 2-(1-carboxy-1-methylethylthio)-3-phenylquinoline, m.p. 144°-6°.

Workup

  1. customat 0°-5°
  2. temperaturethe mixture was heated at 80° for 16 hr
  3. extractionextracted with ethyl acetate (3×25 ml.)
  4. extractionThe ethyl acetate extract
  5. washwas washed with brine (25 ml.)
  6. dry with materialdried (MgSO4)
  7. customThe solvent was evaporated
  8. customthe residual oil was chromatographed on silica (100 g., Merck type 7734)
  9. washeluted
  10. temperaturewith increasing concentrations of ethyl acetate in petroleum ether
  11. customThe eluate obtained with 10% v/v ethyl acetate in petroleum ether
  12. customwas evaporated
  13. customthe solid residue crystallised from cyclohexane

Sources & evidence

ORD record
ord-126c40e8801f4eb9a77adf9d82ff952a
Source dataset
uspto-grants-1984_03
Patent number
US04435405

Reaction notes

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