Allyltributylstannane → 7-Allyl-4-phenylquinoline-2-carbonitrile

HRID 2422567Notes

Reaction equation

HRID 2422567 reaction equation
Cl[C:2]1[CH:11]=[C:10]2[C:5]([C:6]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)=[CH:7][C:8]([C:12]#[N:13])=[N:9]2)=[CH:4][CH:3]=1.[CH2:20]([Sn](CCCC)(CCCC)CCCC)[CH:21]=[CH2:22]>O1CCOCC1>[CH2:22]([C:2]1[CH:11]=[C:10]2[C:5]([C:6]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)=[CH:7][C:8]([C:12]#[N:13])=[N:9]2)=[CH:4][CH:3]=1)[CH:21]=[CH2:20]

Participants

4

Reactant 2

HCID 90628AllyltributylstannaneHCID 597749247-Chloro-4-phenylquinoline-2-carbonitrile

Product 1

HCID 597748917-Allyl-4-phenylquinoline-2-carbonitrile

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a solution of 7-chloro-4-phenylquinoline-2-carbonitrile (3.3 g, 12.5 mmol) in dioxane (120 mL) was added tetrakistriphenylphosphine (3.6 g, 3.1 mmol) and allyltributyltin (11.5 mL, 38 mmol). The mixture was refluxed for 10 h, concentrated and purified on silica gel (eluting with dichloromethane/hexanes, 3:1) to give the title compound. MS (+ESI): 271 (M+H)+.

Workup

  1. temperatureThe mixture was refluxed for 10 h
  2. concentrationconcentrated
  3. custompurified on silica gel (eluting with dichloromethane/hexanes, 3:1)

Sources & evidence

ORD record
ord-6e62ec91f88b452bbfd6a719e9259830
Source dataset
uspto-grants-2011_06
Patent number
US07960409B2

Reaction notes

Loading…