Methyl iodide → Quinoline

HRID 857274Notes

Reaction equation

HRID 857274 reaction equation
Br[C:2]1[CH:3]=[C:4](CS(C)(=O)=O)[CH:5]=[C:6]2[C:11]=1[N:10]=[CH:9][CH:8]=[CH:7]2.CC(C)([O-])C.[K+].CI>C1COCC1.[NH4+].[Cl-]>[N:10]1[C:11]2[C:6](=[CH:5][CH:4]=[CH:3][CH:2]=2)[CH:7]=[CH:8][CH:9]=1

Participants

6

Reactant 3

HCID 6328Methyl iodide2×HCID 98793738-Bromo-6-[(methanesulfonyl)methyl]quinolineHCID 23665647Potassium tert-butoxide2×

Product 1

HCID 7047Quinoline

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 25517Ammonium ChlorideSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of the 8-bromo-6-methanesulfonylmethyl-quinoline (1.0 eq) from Step 1 in THF (0.1M) at 0° C., was added potassium t-butoxide (1.3 eq; 1M in THF) over 30 min. After 0.5 h at 0° C., MeI (1.6 eq) was added and the resulting reaction mixture was stirred at 0° C. for 2 h. A second portion of potassium t-butoxide (1.0 eq; 1M in THF) was added over 30 min, followed by MeI (1.6 eq). The mixture was stirred at room temperature for 2 h. The mixture was poured in saturated aqueous NH4Cl and extracted with EtOAc (2×). The combined organic extracts were washed with brine, dried over MgSO4, filtered and concentrated. The residue was vigorously stirred in Et2O and the title compound was isolated by filtration as a pale yellow solid.

Workup

  1. customthe resulting reaction mixture
  2. stirringThe mixture was stirred at room temperature for 2 h
  3. extractionextracted with EtOAc (2×)
  4. washThe combined organic extracts were washed with brine
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. stirringThe residue was vigorously stirred in Et2O

Sources & evidence

ORD record
ord-c2d766fd091547e39b968cb85319b13e
Source dataset
uspto-grants-2006_12
Patent number
US07144896B2

Reaction notes

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