Chlorotrimethylsilane → 6-Cyanopyridine-3-carboxylic acid

HRID 1990748Notes

Reaction equation

HRID 1990748 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-43995a307a914deaa7c1d2f3ebb5e20e
Source dataset
uspto-grants-2010_01
Patent number
US07645751B2

Reaction notes

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