1-Methylimidazole → HCID 20158996, compound

HRID 986023Notes

Reaction equation

HRID 986023 reaction equation
C([Li])CCC.[CH3:6][N:7]1[CH:11]=[CH:10][N:9]=[CH:8]1.Br[C:13]1[CH:14]=[C:15]2[C:20](=[CH:21][CH:22]=1)[N:19]=[C:18]([O:23][CH3:24])[CH:17]=[CH:16]2.[Cl-].[NH4+]>CCCCCC.C1COCC1.[Cl-].[Zn+2].[Cl-]>[CH3:6][N:7]1[CH:11]=[CH:10][N:9]=[C:8]1[C:13]1[CH:14]=[C:15]2[C:20](=[CH:21][CH:22]=1)[N:19]=[C:18]([O:23][CH3:24])[CH:17]=[CH:16]2

Participants

8

Reactant 4

HCID 13901-MethylimidazoleHCID 25517Ammonium ChlorideHCID 106575386-Bromo-2-methoxyquinolineHCID 178418339Butyllithium

Product 1

HCID 20158996HCID 20158996, compound

Reagents, catalysts & solvents 3

HCID 3007855ZincchlorideCatalystHCID 8028TetrahydrofuranSolvent3×HCID 8058HexaneSolvent

Procedure

n-Butyl lithium (9 cm3 of a 1.6M solution in hexane) was added at -45° to a stirred solution of 1-methyl-(1H)-imidazole (1.03 cm3) in THF (30 cm3) under nitrogen. After 1.25 hours a solution of anhydrous zinc chloride (1.95 g) in THF (30 cm3) was added dropwise over 5 minutes giving a white precipitate. The mixture was warmed to room temperature, a solution of 6-bromo-2-methoxyquinoline (3 g) and tetrakis (triphenylphosphine) palladium(O) (0.2 g) in THF (20 cm3) was added, and the solution was heated under reflux for 16 hours. Saturated ammonium chloride (2 cm3) was added, the reaction mixture was concentrated in vacuo, and the residue partitioned between chloroform (100 cm3) and a solution of ethylenediaminetetraacetic acid disodium salt (10 g) in water (100 cm3). The aqueous phase was extracted further with chloroform (2×50 cm3) and the combined and dried (MgSO4) extracts were evaporated in vacuo to give a solid, which was chromatographed on silica (Merck "MK 60.9385"), eluting with chloroform:methanol, 19:1 (by volume). The requisite fractions were combined and evaporated in vacuo to afford a foam which was recrystallised from ethyl acetate-hexane to give 6-[1-methyl-(1H)-imidazol-2-yl]-2-methoxyquinoline, m.p. 116.5°-118.5°, (0.517 g).

Workup

  1. customgiving a white precipitate
  2. temperaturethe solution was heated
  3. temperatureunder reflux for 16 hours
  4. concentrationthe reaction mixture was concentrated in vacuo
  5. customthe residue partitioned between chloroform (100 cm3)
  6. extractionThe aqueous phase was extracted further with chloroform (2×50 cm3)
  7. dry with materialdried (MgSO4) extracts
  8. customwere evaporated in vacuo
  9. customto give a solid, which
  10. customwas chromatographed on silica (Merck "MK 60.9385")
  11. washeluting with chloroform
  12. customevaporated in vacuo
  13. customto afford a foam which
  14. customwas recrystallised from ethyl acetate-hexane

Sources & evidence

ORD record
ord-9209e01ede0c4fe89710ca34e3b785a1
Source dataset
uspto-grants-1987_12
Patent number
US04710507

Reaction notes

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