Water → 4-(Furan-3-yl)-7-methylquinoline

HRID 741838Notes

Reaction equation

HRID 741838 reaction equation
Cl[C:2]1[CH:11]=[C:10]2[C:5]([C:6]([C:12]3[CH:16]=[CH:15][O:14][CH:13]=3)=[CH:7][CH:8]=[N:9]2)=[CH:4][CH:3]=1.[CH3:17][Mg+].[Br-].[NH4+].[Cl-].O>CCOCC.Cl[Ni]1(Cl)[P](C2C=CC=CC=2)(C2C=CC=CC=2)CCC[P]1(C1C=CC=CC=1)C1C=CC=CC=1>[O:14]1[CH:15]=[CH:16][C:12]([C:6]2[C:5]3[C:10](=[CH:11][C:2]([CH3:17])=[CH:3][CH:4]=3)[N:9]=[CH:8][CH:7]=2)=[CH:13]1

Participants

7

Reactant 4

HCID 962WaterHCID 25517Ammonium ChlorideHCID 233701707-Chloro-4-(furan-3-yl)quinolineHCID 178418689HCID 178418689, compound

Product 1

HCID 233701774-(Furan-3-yl)-7-methylquinoline

Reagents, catalysts & solvents 2

HCID 178418745HCID 178418745, compoundCatalystHCID 3283Diethyl EtherSolvent

Conditions

Temperature
30 °C

Procedure

To a mixture of 7-chloro-4-(furan-3-yl)quinoline (30.2 g) and [1,3-bis(diphenylphosphino)propane]nickel (II) chloride (7.1 g) in Et2O (950 mL) was added MeMgBr (141 mL, 1.4M in 3:1 THF:toluene) at such a rate to maintain a temperature of 30° C. The mixture was refluxed for 30 min., cooled to 0° C. and saturated NH4Cl (200 mL) was added followed by H2O (100 mL). The layers were separated and the aqueous phase was extracted with EtOAc. The combined organics were washed with NH4OAc buffer, brine, dried (MgSO4) and concentrated. Chromatography (silica gel;EtOAc/hexane (3:7)) provided the title compound as a beige oil.

Workup

  1. temperatureThe mixture was refluxed for 30 min.
  2. temperaturecooled to 0° C.
  3. customThe layers were separated
  4. extractionthe aqueous phase was extracted with EtOAc
  5. washThe combined organics were washed with NH4OAc buffer, brine
  6. dry with materialdried (MgSO4)
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-07cefc43d8834002ad853d126d18dce2
Source dataset
uspto-grants-1996_09
Patent number
US05552437

Reaction notes

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