Sodium Hydroxide → 3-Pyridinecarbonitrile, 2-(chloromethyl)-

HRID 334187Notes

Reaction equation

HRID 334187 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.[OH-].[Na+]>O>[C:9]([C:8]1[C:3]([CH2:2][Cl:14])=[N:4][CH:5]=[CH:6][CH:7]=1)#[N:11]

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 24813Phosphorus oxychloride2×HCID 139295182-(Hydroxymethyl)pyridine-3-carboxamide

Product 1

HCID 469118343-Pyridinecarbonitrile, 2-(chloromethyl)-

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

165.5 g (0.98 mol) of 2-hydroxymethyl-3-pyridinecarboxamide are heated together with 270 ml of phosphorus oxychloride to 90-100° C. for 1 hour. The reaction mixture is cooled to room temperature and subsequently added dropwise to approx. 800 ml of water at 50-60° C. After the phosphorus oxychloride has been hydrolyzed, the mixture is neutralized with sodium hydroxide solution with cooling, in the course of which the product precipitates out. It is filtered off, washed with 300 ml of water and subsequently dried at 35-40° C.

Workup

  1. temperaturewith cooling, in the course of which the product
  2. customprecipitates out
  3. filtrationIt is filtered off
  4. washwashed with 300 ml of water
  5. customsubsequently dried at 35-40° C.

Sources & evidence

ORD record
ord-c75d40948f044a8ea262c3a459630d0a
Source dataset
uspto-grants-2014_11
Patent number
US08883805B2

Reaction notes

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