Propanoic acid, 3-iodo- → Pyridinium, 1-(2-carboxyethyl)-4-(cyanomethyl)-, iodide

HRID 1167396Notes

Reaction equation

HRID 1167396 reaction equation
[C:1]([CH2:3][C:4]1[CH:9]=[CH:8][N:7]=[CH:6][CH:5]=1)#[N:2].[I:10][CH2:11][CH2:12][C:13]([OH:15])=[O:14]>>[I-:10].[C:13]([CH2:12][CH2:11][N+:7]1[CH:8]=[CH:9][C:4]([CH2:3][C:1]#[N:2])=[CH:5][CH:6]=1)([OH:15])=[O:14]

Participants

3

Reactant 2

HCID 8856Propanoic acid, 3-iodo-HCID 41120852-(Pyridin-4-yl)acetonitrile

Product 1

HCID 10381162Pyridinium, 1-(2-carboxyethyl)-4-(cyanomethyl)-, iodideYield 79%

Procedure

4-cyanomethyl-pyridine 475 milligrams (0.004) mole were mixed with 1.0 gram of 3-iodopropionic acid (excess) in 100 ml round bottom flask. The flask was closed using a rubber septem and heated at 130 degrees Celsius using an oil bath for six hours. The flask was allowed to cool to ambient temperature and the reaction product was washed by triturating with ether. Acetone 30 ml was added and kept at room temperaturea for 12 hours. The precipitated product was filtered and washed with acetone, 755 mg (79%) of product was obtained.

Workup

  1. customThe flask was closed
  2. temperatureheated at 130 degrees Celsius
  3. customfor six hours
  4. washthe reaction product was washed
  5. customby triturating with ether
  6. additionAcetone 30 ml was added
  7. filtrationThe precipitated product was filtered
  8. washwashed with acetone

Sources & evidence

ORD record
ord-dd674e888e444df89f6353e06eb97bda
Source dataset
uspto-grants-2003_09
Patent number
US06617458B2

Reaction notes

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