Hydrochloric Acid → HCID 22492686, compound

HRID 1816189Notes

Reaction equation

HRID 1816189 reaction equation
FC(F)(F)S(O[C:7]1[CH:8]=[C:9]2[C:14](=[CH:15][CH:16]=1)[N:13]=[CH:12][CH:11]=[CH:10]2)(=O)=O.C(=O)([O-])[O-].[K+].[K+].O.Cl>C=CCCC.C1COCC1.CN(C=O)C.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH2:15]([C:7]1[CH:8]=[C:9]2[C:14](=[CH:15][CH:16]=1)[N:13]=[CH:12][CH:11]=[CH:10]2)[CH2:16][CH2:7][CH2:8][CH3:9]

Participants

9

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 11430Potassium CarbonateHCID 152903586-Quinolinyl trifluoromethanesulfonate

Product 1

HCID 22492686HCID 22492686, compoundYield 148.9%

Reagents, catalysts & solvents 4

HCID 178418397HCID 178418397, compoundCatalystHCID 6228DimethylformamideSolventHCID 80041-PenteneSolventHCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
5 °C

Procedure

In a 5 liter-three necked flask, 21.8 g (311 mM) of 1-pentene and 170 ml of THF were placed for dissolution, and under stirring in a nitrogen gas stream atmosphere, 673.4 ml of 0.5M-THF solution of 9-BBN(9-borabicyclo[3.3.1]nonane) was added dropwise at −25 to −20° C. over 15 minutes, followed by stirring for 1 hour at −10° C. and further for 3 hours at 5° C. Under stirring on an ice bath, to the reaction mixture, 6.75 g (5.84 mM) of Pd (PPh3)4 was added, and a solution of 79.6 g (287 mM) of 6-trifluoromethylsulfonyloxyquinoline in 1010 ml of DMF (methylformamide) was added dropwise, followed by the addition of 62.1 g of anhydrous potassium carbonate and then stirring for 10 minutes. The system was warmed and stirred at 50-54° C. for 3 hours. After the reaction, the reaction mixture was left standing for cooling and gradually poured into 3 liters of cool water, followed by extraction four times with 500 ml of toluene and washing of the organic layer with water. The organic layer was evaporated or condensed into ca. 1 liter thereof, followed by the addition of HCl so as to provide pH=1 and washing of the water layer (phase) with toluene. The water layer was alkalinized with 10% NaOH to pH=11 and extracted with toluene. The organic layer was dried and evaporated into a black liquid. The black liquid was purified by silica gel column chromatography (eluent: hexane/ethyl acetate=5/1) to obtain 42.6 g (yield: 74.4%) of 6-pentylquinoline.

Workup

  1. additionwas added dropwise at −25 to −20° C. over 15 minutes
  2. additionwas added
  3. stirringstirring for 10 minutes
  4. temperatureThe system was warmed
  5. stirringstirred at 50-54° C. for 3 hours
  6. customAfter the reaction
  7. waitthe reaction mixture was left
  8. temperaturefor cooling
  9. extractionfollowed by extraction four times with 500 ml of toluene
  10. washwashing of the organic layer with water
  11. customThe organic layer was evaporated
  12. customcondensed into ca. 1 liter
  13. customto provide pH=1
  14. washwashing of the water layer (phase) with toluene
  15. extractionextracted with toluene
  16. customThe organic layer was dried
  17. customevaporated into a black liquid
  18. customThe black liquid was purified by silica gel column chromatography (eluent: hexane/ethyl acetate=5/1)

Sources & evidence

ORD record
ord-e3a7c178293b4ad5a52460b4f4c67e0c
Source dataset
uspto-grants-2005_04
Patent number
US06884477B1

Reaction notes

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