3-Cyanopyridine → 2-Methylidenepentanediamide

HRID 839503Notes

Reaction equation

HRID 839503 reaction equation
C(N)(=[O:8])C1C=CC=CC=1.C(#N)C1C=CC=NC=1.[C:18]([NH2:26])(=[O:25])[C:19]1[CH:24]=[CH:23][CH:22]=[N:21][CH:20]=1.C=C(CCC#N)C#N>C(#N)C1C=CC=CC=1.O.N1C=CC=CC=1>[CH2:20]=[C:19]([CH2:24][CH2:23][C:22]([NH2:21])=[O:8])[C:18]([NH2:26])=[O:25]

Participants

8

Reactant 4

HCID 793-CyanopyridineHCID 936NicotinamideHCID 2331BenzamideHCID 740802,4-Dicyano-1-butene

Product 1

HCID 203233372-Methylidenepentanediamide

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 1049PyridineSolventHCID 7505BenzonitrileSolvent

Conditions

Temperature
120 °C

Procedure

Into 10 ml stainless steel tubes were charged 0.1 mmole RhCl3.3H2O, 0.4 mmole TLTTP, 4 ml pyridine, 1-2 g of nitrile and a stoichiometric equivalent amount of water. The tubes were pressurized to 150 psig with nitrogen and heated at 120° C. for 17 hours and then the products were determined. In this manner, benzonitrile was converted to benzamide and nicotinonitrile was converted to nicotinamide. These reactions were repeated on a scale up of about 10-times using methyleneglutaronitrile as the nitrile, 115° C. for 27 hours and a nitrogen pressure of 210 psig to produce 2-methyleneglutaramide.

Workup

  1. customfor 27 hours

Sources & evidence

ORD record
ord-923297d1f2d349f8b077a99ad3f519a6
Source dataset
uspto-grants-1978_06
Patent number
US04096149

Reaction notes

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