2-Chloroquinoline → HCID 22241416, compound

HRID 892204Notes

Reaction equation

HRID 892204 reaction equation
[H-].[Na+].[CH3:3][O:4][CH2:5][CH2:6][O:7][CH2:8][O:9][C:10]1[CH:11]=[C:12]([CH2:16][OH:17])[CH:13]=[CH:14][CH:15]=1.Cl[C:19]1[CH:28]=[CH:27][C:26]2[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=2)[N:20]=1>CS(C)=O.CCOC(C)=O>[CH3:3][O:4][CH2:5][CH2:6][O:7][CH2:8][O:9][C:10]1[CH:11]=[C:12]([CH:13]=[CH:14][CH:15]=1)[CH2:16][O:17][C:19]1[CH:28]=[CH:27][C:26]2[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=2)[N:20]=1

Participants

6

Reactant 3

HCID 119282-ChloroquinolineHCID 24758Sodium hydrideHCID 22241324HCID 22241324, compound

Product 1

HCID 22241416HCID 22241416, compound

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

To a suspension of 60% NaH (44 mg, 1.1 mmol) in DMSO (2 mL) is added dropwise a solution of [3-(2-methoxy-ethoxymethoxy)-phenyl]-methanol (212 mg, 1.0 mmol, example 72) in DMSO (1 mL). Let stir 20 min. then added 2-chloroquinoline (180 mg, 1.1 mmol) and heated to 100° C. for 1 hr. Cooled reaction mixture to room temp. and diluted with EtOAc. The organic layer is washed with sat. NH4Cl soln., brine, dried over MgSO4 and concentrated. The residue is purified by flash chromatography (silica, 25% ethyl acetate in hexanes) to give the title compound as a colorless oil. MS (ESI) 340 (M+H)+.

Workup

  1. temperatureCooled
  2. customreaction mixture to room temp.
  3. washThe organic layer is washed with sat. NH4Cl soln
  4. dry with material, brine, dried over MgSO4
  5. concentrationconcentrated
  6. customThe residue is purified by flash chromatography (silica, 25% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-cd7b1280a85542f693eef5cf1f268e16
Source dataset
uspto-grants-2006_02
Patent number
US07005440B1

Reaction notes

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