Sodium Iodide → HCID 90389349, compound

HRID 1526596Notes

Reaction equation

HRID 1526596 reaction equation
[C:1]([CH2:3][O:4][C:5]1[CH:6]=[C:7]([CH3:15])[C:8]([C:11]([O:13]C)=[O:12])=[N:9][CH:10]=1)#[N:2].[I-].[Na+].Cl[Si](C)(C)C>C(#N)C>[C:1]([CH2:3][O:4][C:5]1[CH:6]=[C:7]([CH3:15])[C:8]([C:11]([OH:13])=[O:12])=[N:9][CH:10]=1)#[N:2]

Participants

5

Reactant 3

HCID 5238Sodium IodideHCID 6397ChlorotrimethylsilaneHCID 90389417HCID 90389417, compound

Product 1

HCID 90389349HCID 90389349, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
70 °C

Procedure

To a solution of methyl 5-(cyanomethoxy)-3-methylpicolinate (0.895 g, 4.34 mmol) and sodium iodide (0.354 ml, 8.68 mmol, Sigma-Aldrich Chemical Company, Inc.) in acetonitrile (4.34 ml) was added chlorotrimethylsilane (1.102 ml, 8.68 mmol, Strem Chemicals, Inc.). The reaction mixture was heated to 70° C. and allowed to stir overnight. The reaction mixture was concentrated under reduced pressure and the residue was diluted with water and extracted with EtOAc. The organic extract was washed with water, 10% sodium thio sulfate solution and dried over MgSO4. The filtrate was concentrated in vacuo to give 5-(cyanomethoxy)-3-methylpicolinic acid which was used without further purification. MS m/z=192.9 [M+H]+. Calculated for C9H8N2O3: 192.03

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. additionthe residue was diluted with water
  3. extractionextracted with EtOAc
  4. extractionThe organic extract
  5. washwas washed with water, 10% sodium thio sulfate solution
  6. dry with materialdried over MgSO4
  7. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-4a9192eefb3b401d9dab3276e057f268
Source dataset
uspto-grants-2015_07
Patent number
US09085576B2

Reaction notes

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