Dimethylcarbamoyl Chloride → 7-Methylquinoline-2-carbonitrile

HRID 922747Notes

Reaction equation

HRID 922747 reaction equation
[CH3:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][CH:8]=[N+:9]2[O-])=[CH:4][CH:3]=1.[Si]([C:17]#[N:18])(C)(C)C.CN(C)C(Cl)=O>C(Cl)Cl>[CH3:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][C:8]([C:17]#[N:18])=[N:9]2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 6598Dimethylcarbamoyl ChlorideHCID 82115Trimethylsilyl cyanideHCID 232711687-Methylquinoline 1-oxide

Product 1

HCID 107971837-Methylquinoline-2-carbonitrileYield 71.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 7-methylquinoline N-oxide (1-2, 246 g, 1.54 mol, 1.0 equiv) in methylene chloride (5 L, 0.31 M) was added TMS-CN (414 ml, 3.1 mol., 2 equiv.) followed by dimethylcarbamoyl chloride (284 ml, 3.1 mol. 2 equiv), and the resulting mixture was stirred at room temperature overnight. The solution was quenched with saturated sodium bicarbonate, diluted with water, and extracted with dichloromethane. The combined organic layers were dried over MgSO4, filtered and the solvent removed to give 260 g of crude material which was recrystallized from methanol to give 186 g of 7-methylquinoline-2-carbonitrile (1-3) in two crops. LRMS m/z (M+H)+ 169.1 found, 169.2 required.

Workup

  1. customThe solution was quenched with saturated sodium bicarbonate
  2. additiondiluted with water
  3. extractionextracted with dichloromethane
  4. dry with materialThe combined organic layers were dried over MgSO4
  5. filtrationfiltered
  6. customthe solvent removed
  7. customto give 260 g of crude material which
  8. customwas recrystallized from methanol

Sources & evidence

ORD record
ord-302d2c98aa4b40999f1cb5527b3008a6
Source dataset
uspto-grants-2016_03
Patent number
US09278960B2

Reaction notes

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