4-Pyridinepropaneamide → 4-Pyridinepropanenitrile

HRID 364717

Reaction equation

HRID 364717 reaction equation
[N:1]1[CH:6]=[CH:5][C:4]([CH2:7][CH2:8][C:9]([NH2:11])=O)=[CH:3][CH:2]=1>O=P(Cl)(Cl)Cl>[C:9]([CH2:8][CH2:7][C:4]1[CH:5]=[CH:6][N:1]=[CH:2][CH:3]=1)#[N:11]

Participants

3

Reactant 1

HCID 37782334-Pyridinepropaneamide

Product 1

HCID 73304614-PyridinepropanenitrileYield 77%

Reagents, catalysts & solvents 1

HCID 24813Phosphorus oxychlorideSolvent

Procedure

A mixture of 3-(4-pyridyl)-propionamide (7.1 g, 0.47M) in POCl3 (25 ml) was heated at about 100° to about 110° C. for 2 hrs. The excess of POCl3 was removed in vacuo from the reaction. Thereafter water was added and the resulting solution was basified with aqueous Na2CO3 sol. and extracted with CHCl3. The combined extracts were dried over Na2SO4 and concentrated and distilled at 1 mmHg/118°-120° C. to give 4(2-cyanoethyl)pyridine as an oil (4.8 g, 77% yield).

Workup

  1. temperaturewas heated at about 100° to about 110° C. for 2 hrs
  2. customThe excess of POCl3 was removed in vacuo from the reaction
  3. additionThereafter water was added
  4. extractionextracted with CHCl3
  5. dry with materialThe combined extracts were dried over Na2SO4
  6. concentrationconcentrated
  7. distillationdistilled at 1 mmHg/118°-120° C.

Sources & evidence

ORD record
ord-f4fbddcfe74a42fbb1968b95d9344d80
Source dataset
uspto-grants-1986_08
Patent number
US04605744

Linked notes

Loading…