HCID 21865559, compound → Quinoline

HRID 857270Notes

Reaction equation

HRID 857270 reaction equation
C([C:4]1[CH:5]=[C:6]2[C:11](=[C:12](C3C=CC=C(SC)C=3)[CH:13]=1)[N:10]=[CH:9][CH:8]=[CH:7]2)(C)C.OOS([O-])=O.[K+]>CO.O.C([O-])(O)=O.[Na+]>[N:10]1[C:11]2[C:6](=[CH:5][CH:4]=[CH:13][CH:12]=2)[CH:7]=[CH:8][CH:9]=1

Participants

6

Reactant 2

HCID 21865559HCID 21865559, compoundHCID 23707502Potassium hydroxy sulfite

Product 1

HCID 7047Quinoline

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 516892Sodium BicarbonateSolvent

Procedure

To a solution of the 6-isopropyl-8-(3-methylsulfanyl-phenyl)-quinoline from the previous Step 1 (0.84 g) in MeOH (0.35M) at 0° C. was added a solution of Oxone (0.5 eq) in water (0.18M). The resulting mixture was stirred for 30 min, then poured in saturated aqueous NaHCO3 and extracted with EtOAc (2×). The combined organic extracts were washed with brine, dried over MgSO4, filtered and concentrated. The residual oil was dissolved in TFAA (0.2M), stirred at 40° C. for 30 min and finally concentrated. The residual oil was dissolved in excess NEt3:MeOH (1:1) and concentrated. The operation was repeated twice to afford the title compound as a yellow oil which was used as such.

Workup

  1. extractionextracted with EtOAc (2×)
  2. washThe combined organic extracts were washed with brine
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. dissolutionThe residual oil was dissolved in TFAA (0.2M)
  7. stirringstirred at 40° C. for 30 min
  8. concentrationfinally concentrated
  9. dissolutionThe residual oil was dissolved in excess NEt3:MeOH (1:1)
  10. concentrationconcentrated

Sources & evidence

ORD record
ord-317e4aa2a411466899a712338a66a904
Source dataset
uspto-grants-2006_12
Patent number
US07144896B2

Reaction notes

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