Iodine → 6-Formylpyridine-3-carbonitrile

HRID 1095442Notes

Reaction equation

HRID 1095442 reaction equation
[CH3:1][C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][N:3]=1.II.CSC.C(=O)(O)[O-:16].[Na+]>CS(C)=O>[CH:1]([C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][N:3]=1)=[O:16]

Participants

6

Reactant 4

HCID 807IodineHCID 1068Dimethyl SulfideHCID 2819956-Methylpyridine-3-carbonitrileHCID 516892Sodium Bicarbonate

Product 1

HCID 213641446-Formylpyridine-3-carbonitrileYield 50%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
150 °C

Procedure

A mixture of 6-methylnicotinonitrile (10.0 g, 84.6 mmol) and iodine (20.0 g, 78.8 mmol) in dimethylsulfoxide (150 mL) was heated at 150° C. under nitrogen for 20 minutes (reaction exhaust was scrubbed with bleach to remove dimethyl sulfide). After cooling to room temperature saturated aqueous sodium bicarbonate (200 mL) was added carefully and the resulting mixture was extracted with toluene (3×100 mL). The combined organic extracts were washed with brine, dried (MgSO4) and evaporated to give the desired product as an orange oil (5.65 g, 50%) which was used without further purification. 1H NMR (CDCl3, 400 MHz) δ 8.06 (1H, d), 8.17 (1H, dd), 9.05 (1H, d), 10.12 (1H, s).

Workup

  1. additionwas added carefully
  2. extractionthe resulting mixture was extracted with toluene (3×100 mL)
  3. washThe combined organic extracts were washed with brine
  4. dry with materialdried (MgSO4)
  5. customevaporated

Sources & evidence

ORD record
ord-87d452752d8949999605a56994248e10
Source dataset
uspto-grants-2012_03
Patent number
US08138188B2

Reaction notes

Loading…