Water → 3-Pyridinecarbonitrile, 2-(chloromethyl)-

HRID 44903Notes

Reaction equation

HRID 44903 reaction equation
O[CH2:2][C:3]1[C:8]([C:9]([NH2:11])=O)=[CH:7][CH:6]=[CH:5][N:4]=1.P(Cl)(Cl)([Cl:14])=O.O.[OH-].[Na+]>C(#N)C.C1(C)C=CC=CC=1>[C:9]([C:8]1[C:3]([CH2:2][Cl:14])=[N:4][CH:5]=[CH:6][CH:7]=1)#[N:11]

Participants

7

Reactant 4

HCID 962WaterHCID 14798Sodium HydroxideHCID 24813Phosphorus oxychlorideHCID 139295182-(Hydroxymethyl)pyridine-3-carboxamide

Product 1

HCID 469118343-Pyridinecarbonitrile, 2-(chloromethyl)-

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 6342AcetonitrileSolvent

Conditions

Temperature
78 °C

Procedure

20.0 g (131.45 mmol) of 2-hydroxymethyl-3-pyridinecarboxamide are suspended in 110 ml of acetonitrile and heated to 78° C. Within 15 minutes, 60.65 g (395.52 mmol) of phosphorus oxychloride are metered in and the mixture is heated to 81° C. for 2 hours. After cooling at 22° C., the reaction mixture is stirred into 200 ml of water at 40° C. After 100 ml of toluene have been added, the mixture is neutralized with sodium hydroxide solution with cooling. After phase separation, the organic phase is washed with 100 ml of water. Removal of the organic phase and evaporation of the solvent under reduced pressure gives rise initially to an oily residue which crystallizes on standing.

Workup

  1. temperatureis heated to 81° C. for 2 hours
  2. temperatureAfter cooling at 22° C.
  3. temperaturewith cooling
  4. customAfter phase separation
  5. washthe organic phase is washed with 100 ml of water
  6. customRemoval of the organic phase and evaporation of the solvent under reduced pressure
  7. customgives rise initially to an oily residue which
  8. customcrystallizes

Sources & evidence

ORD record
ord-fe2111bb89b6400580ce79077910f589
Source dataset
uspto-grants-2013_09
Patent number
US08541450B2

Reaction notes

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