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

HRID 44902Notes

Reaction equation

HRID 44902 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-ea79b23d79d04a57bcd85d8bc5c31064
Source dataset
uspto-grants-2013_09
Patent number
US08541450B2

Reaction notes

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