Chlorotrimethylsilane → 6-Cyanopyridine-3-carboxylic acid

HRID 1717485Notes

Reaction equation

HRID 1717485 reaction equation
[C:1]([OH:10])(=[O:9])[C:2]1[CH:7]=[CH:6][CH:5]=[N+:4]([O-])[CH:3]=1.[C-]#N.[Na+].[CH2:14]([N:16](CC)CC)C.C[Si](Cl)(C)C>CN(C=O)C>[C:14]([C:5]1[CH:6]=[CH:7][C:2]([C:1]([OH:10])=[O:9])=[CH:3][N:4]=1)#[N:16]

Participants

6

Reactant 4

HCID 6397ChlorotrimethylsilaneHCID 8471TriethylamineHCID 8929Sodium CyanideHCID 16976Oxiniacic Acid

Product 1

HCID 27611086-Cyanopyridine-3-carboxylic acidYield 22%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
110 °C

Procedure

To a solution of the nicotinic acid N-oxide (51 g, 0.37 mol) in 1.2 L of DMF, NaCN (54 g, 1.1 mol) was added, followed by triethylamine (255 mL, 1.83 mol) and TMSCl (185 mL). The reaction mixture was stirred at 110° C. for 10 h, filtered and the filtrate was concentrated. The residue was dissolved in 100 mL of 2N HCl and extracted with methylene chloride. The organic layers were combined, concentrated and recrystallised from water to yield 12 g (22%) of the product.

Workup

  1. filtrationfiltered
  2. concentrationthe filtrate was concentrated
  3. dissolutionThe residue was dissolved in 100 mL of 2N HCl
  4. extractionextracted with methylene chloride
  5. concentrationconcentrated
  6. customrecrystallised from water

Sources & evidence

ORD record
ord-e7bc7da5f7324e36a6c29b9e1568f984
Source dataset
uspto-grants-2010_09
Patent number
US07803954B2

Reaction notes

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