2-(Chloromethyl)quinoline → HCID 18971781, compound

HRID 2395401Notes

Reaction equation

HRID 2395401 reaction equation
[H-].[Na+].[CH:3]12[CH2:9][CH:6]([CH2:7][CH2:8]1)[CH2:5][CH:4]2[O:10][C:11]1[CH:12]=[C:13]([CH:19]2[CH2:24][NH:23][C:22](=[O:25])[NH:21][CH2:20]2)[CH:14]=[CH:15][C:16]=1[O:17][CH3:18].Cl[CH2:27][C:28]1[CH:37]=[CH:36][C:35]2[C:30](=[CH:31][CH:32]=[CH:33][CH:34]=2)[N:29]=1>CN(C)C=O.O>[CH:3]12[CH2:9][CH:6]([CH2:7][CH2:8]1)[CH2:5][CH:4]2[O:10][C:11]1[CH:12]=[C:13]([CH:19]2[CH2:24][N:23]([CH2:27][C:28]3[CH:37]=[CH:36][C:35]4[C:30](=[CH:31][CH:32]=[CH:33][CH:34]=4)[N:29]=3)[C:22](=[O:25])[N:21]([CH2:27][C:28]3[CH:37]=[CH:36][C:35]4[C:30](=[CH:31][CH:32]=[CH:33][CH:34]=4)[N:29]=3)[CH2:20]2)[CH:14]=[CH:15][C:16]=1[O:17][CH3:18]

Participants

6

Reactant 3

HCID 203942-(Chloromethyl)quinolineHCID 24758Sodium hydrideHCID 9839925HCID 9839925, compound

Product 1

HCID 18971781HCID 18971781, compoundYield 10.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

NaH (63 mg, 1.58 mmol, 1.0 eq, 60% oil dispersion) was added to a mixture of (0.500 g, 1.58 mmol, 1.0 eq) 5-[3-(bicyclo[2.2.1]hept-2-yloxy)4-methoxyphenyl]tetra-hydro-2(1H)-pyrimidinone and (0.279 g, 1.58 mmol, 1.0 eq) 2-chloromethylquinoline in 12 ml of anhydrous dimethylformamide. After stirring for 18 hours at room temperature, the reaction mixture was diluted with 250 ml of H2O and extracted with ethyl acetate. The ethyl acetate extract was washed once with H2O, once with brine, dried over Na2SO4, and concentrated in vacuo. The residue was chromatographed on a silica gel column, eluting with 21/2% CH3OH-CH2Cl2 to yield 50 mg of a solid, which was recrystallized from ethyl acetate-hexane to afford 45 mg, 5%, of a white crystalline solid. M.P.: 135°-136° C.

Workup

  1. extractionextracted with ethyl acetate
  2. extractionThe ethyl acetate extract
  3. washwas washed once with H2O, once with brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated in vacuo
  6. customThe residue was chromatographed on a silica gel column
  7. washeluting with 21/2% CH3OH-CH2Cl2

Sources & evidence

ORD record
ord-b35cb90781054ae0b9cfd9822ce15f42
Source dataset
uspto-grants-1998_09
Patent number
US05814651

Reaction notes

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