1-Bromo-3-chloropropane → HCID 66961254, compound

HRID 68999Notes

Reaction equation

HRID 68999 reaction equation
[C:1](=[O:4])([O-])[O-].[K+].[K+].[OH:7][C:8]1[CH:9]=[C:10]2[C:15](=[CH:16][CH:17]=1)[N:14]=[C:13](OC)[CH:12]=[CH:11]2.[Cl:20][CH2:21][CH2:22][CH2:23]Br>C(#N)C.O>[Cl:20][CH2:21][CH2:22][CH2:23][O:7][C:8]1[CH:9]=[C:10]2[C:15](=[CH:16][CH:17]=1)[N:14]([CH3:13])[C:1](=[O:4])[CH:12]=[CH:11]2

Participants

6

Reactant 3

HCID 80061-Bromo-3-chloropropaneHCID 11430Potassium CarbonateHCID 450911926-Hydroxy-2-methoxyquinoline

Product 1

HCID 66961254HCID 66961254, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 6342AcetonitrileSolvent

Procedure

Potassium carbonate (0.829 g) was dissolved in acetonitrile (10 ml) and water (10 ml), and 6-hydroxy-2-methoxyquinoline (0.875 g) and 1-chloro-3-bromopropane (1.48 ml) was added thereto, and the mixture was stirred while heating under reflux for 4 hours. The reaction mixture was condensed under reduced pressure. Water was added to the residue, followed by extraction using ethyl acetate. The organic layer was dried with sodium sulfate, and was condensed under reduced pressure. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=1:1). The purified product was condensed to dryness under reduced pressure to give the title compound (1.107 g) as a white powder.

Workup

  1. temperaturewhile heating
  2. temperatureunder reflux for 4 hours
  3. customcondensed under reduced pressure
  4. extractionfollowed by extraction
  5. dry with materialThe organic layer was dried with sodium sulfate
  6. customcondensed under reduced pressure
  7. customThe residue was purified by silica gel column chromatography (hexane:ethyl acetate=1:1)
  8. customcondensed to dryness under reduced pressure

Sources & evidence

ORD record
ord-6af2b31558e94fa4a1dc4925a91fd34a
Source dataset
uspto-grants-2014_09
Patent number
US08822453B2

Reaction notes

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