Hydrochloric Acid → HCID 57061813, compound

HRID 2187358Notes

Reaction equation

HRID 2187358 reaction equation
[CH3:1][O:2][C:3]([C:5]1[C:14]2[C:9](=[C:10](Br)[CH:11]=[CH:12][CH:13]=2)[N:8]=[CH:7][CH:6]=1)=[O:4].[CH2:16]([O:18]C([Sn](CCCC)(CCCC)CCCC)=C)[CH3:17].Cl.O>O1CCOCC1.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>[CH3:1][O:2][C:3]([C:5]1[C:14]2[C:9](=[C:10]([C:16](=[O:18])[CH3:17])[CH:11]=[CH:12][CH:13]=2)[N:8]=[CH:7][CH:6]=1)=[O:4]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 619414Stannane, tributyl(1-ethoxyethenyl)-HCID 54001655Methyl 8-bromoquinoline-4-carboxylate

Product 1

HCID 57061813HCID 57061813, compound

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 312751,4-DioxaneSolvent

Procedure

8-Bromo4-quinoline carboxylic acid methyl ester, D16 (E. R. Buchman et al., J. Amer. Chem. Soc., 1946, 68, 2692), (0.712 g), (1-ethoxyvinyl)tributyltin (1.60 g) and tetrakis(triphenylphosphine)palladium (O) in 1,4-dioxane (50 ml) were heated at reflux for 16 h. The reaction mixture was cooled to ambient temperature, HCl (5M, 1 ml) and water (15 ml) added and the resulting mixture stirred for 3 h. The solvent was removed at reduced pressure, the residue suspended in EtOAc and the solid removed by filtration. The organic phase was washed with saturated sodium bicarbonate, dried (Na2SO4), removal of the solvent under reduced pressure gave a dark oil which was chromatographed (silica gel, hexane diethyl ether) to give the title compound (0.500 g).

Workup

  1. temperatureat reflux for 16 h
  2. customThe solvent was removed at reduced pressure
  3. customthe solid removed by filtration
  4. washThe organic phase was washed with saturated sodium bicarbonate
  5. customdried
  6. custom(Na2SO4), removal of the solvent under reduced pressure
  7. customgave a dark oil which
  8. customwas chromatographed (silica gel, hexane diethyl ether)

Sources & evidence

ORD record
ord-eb6945b5bbd84747b04d102f8ec6b58e
Source dataset
uspto-grants-2002_06
Patent number
US06410529B1

Reaction notes

Loading…