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

HRID 424459Notes

Reaction equation

HRID 424459 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) 2-hydroxymethyl-3-pyridinecarboxamide are heated together with 270 ml of phosphorus oxychloride for 1 hour at 90-100° C. The reaction mixture is cooled to ambient temperature and then added dropwise to about 800 ml of water at a temperature of 50-60° C. After hydrolysis of the phosphorus oxychloride the mixture is neutralised while being cooled with sodium hydroxide solution, whereupon the product is precipitated. It is filtered off, washed with 300 ml of water and then dried at 35-40° C.

Workup

  1. customis precipitated
  2. filtrationIt is filtered off
  3. washwashed with 300 ml of water
  4. customdried at 35-40° C.

Sources & evidence

ORD record
ord-9bebb1c3023d4dc3bedd5a1c0764fe8f
Source dataset
uspto-grants-2012_01
Patent number
US08106060B2

Reaction notes

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