Nicotinamide → 3-(Isocyanatomethyl)pyridine

HRID 261017Notes

Reaction equation

HRID 261017 reaction equation
[C:1]([NH2:9])(=O)[C:2]1[CH:7]=[CH:6][CH:5]=[N:4][CH:3]=1.C(Cl)(=O)[C:11](Cl)=[O:12]>C(Cl)CCl>[CH2:1]([N:9]=[C:11]=[O:12])[C:2]1[CH:7]=[CH:6][CH:5]=[N:4][CH:3]=1

Participants

4

Reactant 2

HCID 936NicotinamideHCID 65578Oxalyl chloride

Product 1

HCID 154546703-(Isocyanatomethyl)pyridine

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

To a mixture of nicotinamide (24.4 g., 0.20 mole) and dry ethylene dichloride (2500 ml.) is added oxalyl chloride (38.1 g., 0.30 mole). The mixture is then heated to reflux for 4.5 hours and then cooled to room temperature. It is filtered to give a clear pale orange solution of nicotinyl isocyanate which is used directly in the next step.

Workup

  1. temperatureThe mixture is then heated
  2. temperatureto reflux for 4.5 hours
  3. filtrationIt is filtered

Sources & evidence

ORD record
ord-410bd78b19be458b84b0eafe57e0af26
Source dataset
uspto-grants-1979_08
Patent number
US04163784

Reaction notes

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