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

HRID 2113113Notes

Reaction equation

HRID 2113113 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-f208dcec503f4fbc9240dbbb02f64b8c
Source dataset
uspto-grants-2009_04
Patent number
US07524873B2

Reaction notes

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