Triphenylphosphine → HCID 21948811, compound

HRID 2182681Notes

Reaction equation

HRID 2182681 reaction equation
Cl[C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][C:8]=2[N+:12]([O-:14])=[O:13])[N:3]=1.[C:15]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=C[CH:16]=1.C(C([Sn])=C(CCCC)CCCC)CCC>C1(C)C=CC=CC=1>[N+:12]([C:8]1[CH:7]=[CH:6][CH:5]=[C:4]2[C:9]=1[CH:10]=[CH:11][C:2]([CH:15]=[CH2:16])=[N:3]2)([O-:14])=[O:13]

Participants

5

Reactant 3

HCID 11776TriphenylphosphineHCID 3192512-Chloro-5-nitroquinolineHCID 53438229Tri(butyl)vinyltin

Product 1

HCID 21948811HCID 21948811, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

5.06 g (24.5 mmol) of 2-chloro-5-nitroquinoline, 1.26 g (4.9 mmol) of triphenylphosphine and 8.0 g (25.2 mmol) of tri-n-butylvinyltin are dissolved in 60 ml of toluene. After adding 2.75 g (2.5 mmol) of tris(dibenzylidenacetone)dipalladium, the reaction mixture is allowed to reflux for 20 hours. Then, it is filtered on Celite and washed with ethyl acetate. The filtrate is mixed with saturated ammonium chloride solution. It is extracted with ethyl acetate, and the combined organic phases are dried on sodium sulfate. After the solvent is removed in a vacuum and after subsequent chromatography on silica gel with hexane-ethyl acetate (5-20%), 3.05 g (62% of theory) of the product is obtained.

Workup

  1. temperatureto reflux for 20 hours
  2. filtrationThen, it is filtered on Celite
  3. washwashed with ethyl acetate
  4. additionThe filtrate is mixed with saturated ammonium chloride solution
  5. extractionIt is extracted with ethyl acetate
  6. customthe combined organic phases are dried on sodium sulfate
  7. customAfter the solvent is removed in a vacuum
  8. customafter subsequent chromatography on silica gel with hexane-ethyl acetate (5-20%), 3.05 g (62% of theory) of the product is obtained

Sources & evidence

ORD record
ord-3dd56155dd6242aa973a62e8d81b65d3
Source dataset
uspto-grants-2005_05
Patent number
US06897224B2

Reaction notes

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