Methyl iodide → Quinoline

HRID 857278Notes

Reaction equation

HRID 857278 reaction equation
Br[C:2]1[CH:3]=[C:4](CC#N)[CH:5]=[C:6]2[C:11]=1[N:10]=[CH:9][CH:8]=[CH:7]2.CI.CC(C)([O-])C.[K+]>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 iodideHCID 21865581HCID 21865581, compoundHCID 23665647Potassium tert-butoxide

Product 1

HCID 7047Quinoline

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 25517Ammonium ChlorideSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of (8-bromo-quinolin-6-yl)-acetonitrile from Step 1 (1.0 eq) in THF (0.12M) at −78° C., was added MeI (2.3 eq) followed by potassium t-butoxide (2.3 eq). After 2 h at −78° C., the resulting mixture was warmed to 0° C. and was poured in saturated aqueous NH4Cl, then extracted with EtOAc (2×). The combined organic extracts were washed with brine, dried over MgSO4, filtered and concentrated. Flash chromatography (Hex:EtOAc, 3:1) afforded the title compound as a white solid.

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

Sources & evidence

ORD record
ord-dd83d1cb475f424f945de8e7c1f797fd
Source dataset
uspto-grants-2006_12
Patent number
US07144896B2

Reaction notes

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