Ethylene Glycol → HCID 50877447, compound

HRID 1890922Notes

Reaction equation

HRID 1890922 reaction equation
[H-].[Na+].[CH2:3]([OH:6])[CH2:4][OH:5].Cl[C:8]1[C:17]2[C:12](=[CH:13][CH:14]=[C:15]([Br:18])[CH:16]=2)[N:11]=[CH:10][CH:9]=1>CN(C=O)C>[Br:18][C:15]1[CH:16]=[C:17]2[C:12](=[CH:13][CH:14]=1)[N:11]=[CH:10][CH:9]=[C:8]2[O:5][CH2:4][CH2:3][OH:6]

Participants

5

Reactant 3

HCID 174Ethylene GlycolHCID 24758Sodium hydride2×HCID 51395376-Bromo-4-chloroquinoline

Product 1

HCID 50877447HCID 50877447, compoundYield 57%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a suspension of sodium hydride (60% suspension, 40 mg, 0.99 mmol) in DMF (3 mL) under nitrogen atmosphere was added ethylene glycol dropwise. The reaction mixture was stirred for 20 min before adding 4-chloro-6-bromoquinoline (200 mg, 0.825 mmol) in one portion. The reaction mixture was stirred at 90° C. for 22 h. Another 20 mg of sodium hydride was added after 16 h. The mixture was cooled to room temperature and concentrated in vacuo. The residue was dissolved in methanol and the solution was adsorbed on silica gel. Purification by flash chromatography on silica gel using a gradient of 0-10% methanol/dichloromethane afforded 127 mg of 2-(6-bromo-quinolin-4-yloxy)-ethanol as a white solid (57% yield): 1H NMR (DMSO-d6) δ 3.93 (q, 2H), 4.32 (t, 2H), 5.21 (t, 1H), 7.14 (d, 1H), 7.94 (m, 2H), 8.50 (d, 1H), 8.82 (d, 1H); MS (m/z) 268, 270 [M+H]+.

Workup

  1. stirringThe reaction mixture was stirred at 90° C. for 22 h
  2. concentrationconcentrated in vacuo
  3. dissolutionThe residue was dissolved in methanol
  4. customPurification by flash chromatography on silica gel using a gradient of 0-10% methanol/dichloromethane

Sources & evidence

ORD record
ord-a5bf4f9bbc6246f38b8d7d4876d63b26
Source dataset
uspto-grants-2013_08
Patent number
US08507489B2

Reaction notes

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