Trimethylsilyl cyanide → 6-Chloro-7-methoxyquinoline-2-carbonitrile

HRID 579334Notes

Reaction equation

HRID 579334 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[O:12][CH3:13])[N+:8]([O-])=[CH:7][CH:6]=[CH:5]2.C[Si]([C:19]#[N:20])(C)C>C(#N)C>[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[O:12][CH3:13])[N:8]=[C:7]([C:19]#[N:20])[CH:6]=[CH:5]2

Participants

4

Reactant 2

HCID 82115Trimethylsilyl cyanideHCID 867271566-Chloro-7-methoxyquinoline 1-oxide

Product 1

HCID 867271556-Chloro-7-methoxyquinoline-2-carbonitrileYield 76.9%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
80 °C

Procedure

A 50 mL flask containing acetonitrile (6.0 mL) was charged with 6-chloro-7-methoxyquinoline 1-oxide (0.25 g, 1.19 mmol), TEA (0.33 mL, 2.39 mmol), and trimethylsilyl cyanide (0.48 mL, 3.58 mmol). The reaction mixture was heated at 80° C. for 2 h, cooled to room temperature and concentrated in vacuo. The residue was basified using saturated Na2CO3 and the product was extracted with DCM. The organic layer was dried with MgSO4, filtered and concentrated in vacuo to afford 6-chloro-7-methoxyquinoline-2-carbonitrile (0.20 g) MS [M+H+]=219.4.

Workup

  1. temperaturecooled to room temperature
  2. concentrationconcentrated in vacuo
  3. extractionthe product was extracted with DCM
  4. dry with materialThe organic layer was dried with MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-09de80e0cb474728bfacc03194212818
Source dataset
uspto-grants-2015_05
Patent number
US09040712B2

Reaction notes

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