1-Bromo-3-chloropropane → 4-Chloro-7-(3-chloropropoxy)-6-methoxyquinoline

HRID 1925376Notes

Reaction equation

HRID 1925376 reaction equation
[Cl:1][C:2]1[C:11]2[C:6](=[CH:7][C:8]([OH:14])=[C:9]([O:12][CH3:13])[CH:10]=2)[N:5]=[CH:4][CH:3]=1.Br[CH2:16][CH2:17][CH2:18][Cl:19].C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[Cl:1][C:2]1[C:11]2[C:6](=[CH:7][C:8]([O:14][CH2:16][CH2:17][CH2:18][Cl:19])=[C:9]([O:12][CH3:13])[CH:10]=2)[N:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 80061-Bromo-3-chloropropaneHCID 11430Potassium CarbonateHCID 1355837314-Chloro-6-methoxyquinolin-7-ol

Product 1

HCID 675200294-Chloro-7-(3-chloropropoxy)-6-methoxyquinoline

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 4-chloro-6-methoxyquinolin-7-ol (5.7 g, 0.027 mole) and 1-bromo-3-chloropropane (13.2 mL, 0.14 mole) in DMF (150 mL), was added potassium carbonate (30 g, 0.27 mole). The mixture was stirred at RT for 20 h. The mixture was concentrated in vacuo then diluted with H2O (100 mL). The mixture was extracted with EtOAc (3×50 mL) and the organic extracts were washed with H2O and brine. The organic phase was dried over MgSO4, filtered, and concentrated in vacuo. The resulting residue was purified by silica gel column chromatography (5% MeOH/CH2Cl2) to yield the title compounds as a light yellow solid. MS (ESI, pos. ion) m/z: 286 (M+1). Mass Calc'd for C13H13Cl2NO2: 285.0.

Workup

  1. concentrationThe mixture was concentrated in vacuo
  2. additionthen diluted with H2O (100 mL)
  3. extractionThe mixture was extracted with EtOAc (3×50 mL)
  4. washthe organic extracts were washed with H2O and brine
  5. dry with materialThe organic phase was dried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe resulting residue was purified by silica gel column chromatography (5% MeOH/CH2Cl2)

Sources & evidence

ORD record
ord-1f8a5671900b425ebc5d7881f371754f
Source dataset
uspto-grants-2012_05
Patent number
US08178557B2

Reaction notes

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