Dimethylcarbamoyl Chloride → 7-Methyl-4-phenylquinoline-2-carbonitrile

HRID 2422524Notes

Reaction equation

HRID 2422524 reaction equation
[CH3:1][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.C1C=C(Cl)C=C(C(OO)=O)C=1.[CH3:29][N:30](C)C(Cl)=O.C[Si](C#N)(C)C.C([O-])(O)=O.[Na+]>C(Cl)(Cl)Cl>[CH3:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6]([C:12]3[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=3)=[CH:7][C:8]([C:29]#[N:30])=[N:9]2)=[CH:4][CH:3]=1

Participants

7

Reactant 5

HCID 6598Dimethylcarbamoyl ChlorideHCID 70297m-Chloroperbenzoic acidHCID 82115Trimethylsilyl cyanideHCID 516892Sodium BicarbonateHCID 15512350HCID 15512350, compound

Product 1

HCID 574378317-Methyl-4-phenylquinoline-2-carbonitrile

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A solution of 7-methyl-4-phenylquinoline (10.0 g, 41.7 mmol) and m-CPBA (13.5 g, 54.8 mmol) in chloroform (230 mL) was stirred at room temperature for 3 h. The reaction was quenched with saturated aqueous NaHCO3 solution and extracted twice with dichloromethane. The combined organic layers were washed with water, brine, and dried over anhydrous MgSO4. The solvent was removed under reduced pressure and the resulting crude product was dissolved in chloroform (220 mL). N,N-Dimethylcarbamoyl chloride (8.44 mL, 91.4 mmol) and trimethylsilyl cyanide (11.5 mL, 91.4 mmol) were added to this solution and stirred at room temperature for 2 d. Saturated aqueous NaHCO3 solution was added and stirred for 30 min. The organic layer was removed, and the aqueous layer was extracted with dichloromethane. The combined organic layers were washed with water, brine, and 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 8.01 (s, 1H), 7.92 (d, 1H), 7.80 (s, 1H), 7.60-7.67 (m, 6H), 2.63 (s, 3H).

Workup

  1. customThe reaction was quenched with saturated aqueous NaHCO3 solution
  2. extractionextracted twice with dichloromethane
  3. washThe combined organic layers were washed with water, brine
  4. dry with materialdried over anhydrous MgSO4
  5. customThe solvent was removed under reduced pressure
  6. dissolutionthe resulting crude product was dissolved in chloroform (220 mL)
  7. stirringstirred for 30 min
  8. customThe organic layer was removed
  9. extractionthe aqueous layer was extracted with dichloromethane
  10. washThe combined organic layers were washed with water, brine
  11. dry with materialdried over anhydrous MgSO4
  12. customThe solvent was removed under reduced pressure
  13. customthe resulting crude product was used in the next step without further purification

Sources & evidence

ORD record
ord-35635a618e9a432fb362988381ff5387
Source dataset
uspto-grants-2011_06
Patent number
US07960409B2

Reaction notes

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