Hydrochloric Acid → 1-(Quinolin-5-yl)ethan-1-one

HRID 1072238Notes

Reaction equation

HRID 1072238 reaction equation
FC(F)(F)S(O[C:7]1[CH:16]=[CH:15][CH:14]=[C:13]2[C:8]=1[CH:9]=[CH:10][CH:11]=[N:12]2)(=O)=O.[CH:19]([O:21]CCCC)=[CH2:20].C(=O)([O-])[O-].[K+].[K+].C1(P(C2C=CC=CC=2)CCCP(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.Cl>CN(C=O)C.O.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[C:19]([C:7]1[CH:16]=[CH:15][CH:14]=[C:13]2[C:8]=1[CH:9]=[CH:10][CH:11]=[N:12]2)(=[O:21])[CH3:20]

Participants

9

Reactant 5

HCID 313Hydrochloric AcidHCID 8108Butyl vinyl etherHCID 11430Potassium CarbonateHCID 812191,3-Bis(diphenylphosphino)propaneHCID 114714035-Quinolyl trifluoromethanesulfonate

Product 1

HCID 153774961-(Quinolin-5-yl)ethan-1-one

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A degassed solution of 5-trifluoromethanesulphonyloxyquinoline (0.41 g, 1.47 mmol), butyl vinyl ether (0.38 mL, 2.94 mmol), palladium acetate (10 mg, 0.043 mmol), potassium carbonate (0.24 g, 1.76 mmol), 1,3-bis(diphenylphosphino)propane (40 mg, 0.097 mmol) in DMF (3.67 mL) and water (0.88 mL) was heated in a sealed tube at 100° C. for 16 hours. The reaction mixture was then cooled and treated with 1M HCl and the mixture stirred for 30 minutes, then basified and extracted with dichloromethane. The organic layer was then evaporated under reduced pressure to afford the title compound.

Workup

  1. temperatureThe reaction mixture was then cooled
  2. extractionextracted with dichloromethane
  3. customThe organic layer was then evaporated under reduced pressure

Sources & evidence

ORD record
ord-9a3786c98fa54c338d3f81fcce829342
Source dataset
uspto-grants-2005_06
Patent number
US06908935B2

Reaction notes

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