Potassium Carbonate → HCID 19745915, compound

HRID 2253753Notes

Reaction equation

HRID 2253753 reaction equation
Cl.Cl[CH2:3][C:4]1[CH:13]=[CH:12][C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N:5]=1.[OH:14][CH:15]([C:18]1[CH:23]=[CH:22][C:21]([OH:24])=[CH:20][CH:19]=1)[CH2:16]O.C([O-])([O-])=[O:26].[K+].[K+]>CN(C)C=O>[OH:26][C:15]([C:18]1[CH:23]=[CH:22][C:21]([O:24][CH2:3][C:4]2[CH:13]=[CH:12][C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[N:5]=2)=[CH:20][CH:19]=1)([OH:14])[CH3:16]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 30819801-(4-Hydroxyphenyl)ethane-1,2-diolHCID 30838232-(Chloromethyl)quinoline hydrochloride

Product 1

HCID 19745915HCID 19745915, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture containing 2-(chloromethyl)quinoline hydrochloride (2.68 g), 2-hydroxy-2-(4-hydroxyphenyl)ethanol (1.74 g) and anhydrous K2CO3 (4.70 g) was stirred at room temperature in dry N,N-dimethylformamide (DMF) for 3 days. DMF was removed under reduced pressure and the residue was partitioned between CH2Cl2 and water. The aqueous phase was re-extracted with CH2Cl2 and the combined organic phase was washed with brine, dried and concentrated. The title compound was obtained after recrystallization from methanol/ethyl acetate/hexane.

Workup

  1. customDMF was removed under reduced pressure
  2. customthe residue was partitioned between CH2Cl2 and water
  3. extractionThe aqueous phase was re-extracted with CH2Cl2
  4. washthe combined organic phase was washed with brine
  5. customdried
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-322f61f0fdc842f28d55e6d482ded328
Source dataset
uspto-grants-1993_08
Patent number
US05232916

Reaction notes

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