7-Chloro-4-phenylquinoline → HCID 15512350, compound

HRID 2422523Notes

Reaction equation

HRID 2422523 reaction equation
Cl[C:2]1[CH:11]=[C:10]2[C:5]([C:6]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)=[CH:7][CH:8]=[N:9]2)=[CH:4][CH:3]=1.[CH3:18][Mg+].[Br-]>CCOCC>[CH3:18][C:2]1[CH:11]=[C:10]2[C:5]([C:6]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)=[CH:7][CH:8]=[N:9]2)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 113454577-Chloro-4-phenylquinolineHCID 178418689HCID 178418689, compound

Product 1

HCID 15512350HCID 15512350, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a solution of 7-chloro-4-phenylquinoline (10.0 g, 41.7 mmol) and Ni(dppp)2Cl2 (2.26 g, 4.17 mmol) in ether (200 mL) was added dropwise 3.0 M MeMgBr (24.3 mL, 73 mmol) and heated at reflux for 3 h. The reaction mixture was quenched with saturated aqueous NH4Cl solution and extracted with ether. The combined organic layer was washed with water and brine and then dried over anhydrous MgSO4. The solvent was removed under reduced pressure, and the resulting crude product was used in the next step without further purification. 1H NMR (400 MHz, acetone-d6): δ 8.9 (d, 1H), 7.93 (bs, 1H), 7.82 (d, 1H), 7.52-7.62 (m, 5H), 7.43 (dd, 1H), 7.35 (d, 1H), 2.60 (S, 3H).

Workup

  1. temperatureheated
  2. temperatureat reflux for 3 h
  3. customThe reaction mixture was quenched with saturated aqueous NH4Cl solution
  4. extractionextracted with ether
  5. washThe combined organic layer was washed with water and brine
  6. dry with materialdried over anhydrous MgSO4
  7. customThe solvent was removed under reduced pressure
  8. customthe resulting crude product was used in the next step without further purification

Sources & evidence

ORD record
ord-66ed36310b09441990961ed03a297fbb
Source dataset
uspto-grants-2011_06
Patent number
US07960409B2

Reaction notes

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