Acetone → HCID 85854015, compound

HRID 1931473Notes

Reaction equation

HRID 1931473 reaction equation
[Cl:1][C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7]([OH:12])[CH:8]=2)[N:3]=1.CC(C)=O.[F:17][C:18]1[CH:25]=[CH:24][C:21]([CH2:22]Br)=[CH:20][CH:19]=1>O>[Cl:1][C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7]([O:12][CH2:22][C:21]3[CH:24]=[CH:25][C:18]([F:17])=[CH:19][CH:20]=3)[CH:8]=2)[N:3]=1

Participants

5

Reactant 3

HCID 180AcetoneHCID 680214-Fluorobenzyl bromideHCID 221325772-Chloroquinolin-6-ol

Product 1

HCID 85854015HCID 85854015, compoundYield 22%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a stirred solution of 2-chloro-6-hydroxy-quinoline (0.6 g, 3.0 mmol) in acetone (15 ml) potassium carbonate (0.55 g, 4.0 mmol) and 4-fluorobenzylbromide (0.76 g, 4.0 mmol) were added at ambient temperature. Then the reaction mixture was heated to reflux for 3 h. Upon cooling to ambient temperature water was added and the whole mixture extracted twice with ethyl acetate. The combined organic phases were dried on sodium sulfate, filtered and evaporated. Purification of the residue by flash chromatography on silica gel (heptane, ethyl acetate 1:0=>1:4) yielded 2-chloro-6-(4-fluoro-benzyloxy)-quinoline as a white solid (0.19 g, 20%), MS 288.8 [(M+H)+].

Workup

  1. temperatureThen the reaction mixture was heated
  2. temperatureto reflux for 3 h
  3. additionwas added
  4. extractionthe whole mixture extracted twice with ethyl acetate
  5. customThe combined organic phases were dried on sodium sulfate
  6. filtrationfiltered
  7. customevaporated
  8. customPurification of the residue by flash chromatography on silica gel (heptane, ethyl acetate 1:0=>1:4)

Sources & evidence

ORD record
ord-4a1add1bda154322bb85cfba2adb8825
Source dataset
uspto-grants-2012_05
Patent number
US08188284B2

Reaction notes

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