Hexane → HCID 18322221, compound

HRID 1698844Notes

Reaction equation

HRID 1698844 reaction equation
Cl.Br[C:3]1[CH:8]=[CH:7][N:6]=[CH:5][CH:4]=1.C([Li])CCC.CCCCCC.[CH3:20][O:21][C:22]1[CH:23]=[C:24]([CH2:28][CH2:29][N:30]2[C:34](=[O:35])[C:33]3=[CH:36][CH:37]=[CH:38][CH:39]=[C:32]3[C:31]2=[O:40])[CH:25]=[CH:26][CH:27]=1.[Cl-].[NH4+]>[OH-].[Na+].C(OCC)C.O1CCCC1>[OH:35][C:34]1([C:3]2[CH:8]=[CH:7][N:6]=[CH:5][CH:4]=2)[C:33]2[C:32](=[CH:39][CH:38]=[CH:37][CH:36]=2)[C:31](=[O:40])[N:30]1[CH2:29][CH2:28][C:24]1[CH:25]=[CH:26][CH:27]=[C:22]([O:21][CH3:20])[CH:23]=1

Participants

9

Reactant 5

HCID 8058HexaneHCID 25517Ammonium ChlorideHCID 881004-Bromopyridinium chlorideHCID 18322222HCID 18322222, compoundHCID 178418339Butyllithium

Product 1

HCID 18322221HCID 18322221, compound

Reagents, catalysts & solvents 3

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolventHCID 14798Sodium HydroxideSolvent

Conditions

Temperature
-70 °C

Procedure

0.69 g (3.55 mmol) of 4-bromopyridine hydrochloride was initially converted into the free base. To this end, the salt was dissolved in 5 ml of 1 M aqueous sodium hydroxide solution, the solution was extracted three times with diethyl ether and the combined organic phases were dried and evaporated to dryness using a rotary evaporator. The residue was dissolved in 5 ml of absolute diethyl ether and the solution was added dropwise at −70° C. to a mixture of 1.6 M butyllithium solution in n-hexane (3.98 mmol) and 10 ml of absolute diethyl ether. The mixture was stirred at −70° C. for 30 min, and a solution of 0.5 g (1.78 mmol) of N-(2-(3-methoxyphenyl)ethyl)phthalimide in 10 ml of absolute tetrahydrofuran was then added dropwise (color change from yellow to brown). After 1 h, the reaction mixture was allowed to warm to room temperature, admixed with 10 ml of saturated ammonium chloride solution and extracted three times with diethyl ether. The combined organic phases were washed once with saturated sodium chloride solution, dried and evaporated to dryness using a rotary evaporator. Recrystallization of the crystalline residue from diisopropyl ether/ethanol gave a colorless crystalline product. Yield: 0.28 g. M.p.: 190° C.

Workup

  1. extractionthe solution was extracted three times with diethyl ether
  2. customthe combined organic phases were dried
  3. customevaporated to dryness
  4. customa rotary evaporator
  5. dissolutionThe residue was dissolved in 5 ml of absolute diethyl ether
  6. waitAfter 1 h
  7. temperatureto warm to room temperature
  8. extractionextracted three times with diethyl ether
  9. washThe combined organic phases were washed once with saturated sodium chloride solution
  10. customdried
  11. customevaporated to dryness
  12. customa rotary evaporator
  13. customRecrystallization of the crystalline residue from diisopropyl ether/ethanol
  14. customgave a colorless crystalline product

Sources & evidence

ORD record
ord-a914cfbf01bb4845891e78ee7aafcff2
Source dataset
uspto-grants-2002_02
Patent number
US06344468B1

Reaction notes

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