Ammonium Hydroxide → 3-Cyclopentylpropionitrile

HRID 1085069Notes

Reaction equation

HRID 1085069 reaction equation
[CH:1]1([CH2:6][CH2:7][C:8](Cl)=O)[CH2:5][CH2:4][CH2:3][CH2:2]1.[OH-].[NH4+:12]>>[CH:1]1([CH2:6][CH2:7][C:8]#[N:12])[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

3

Reactant 2

HCID 14923Ammonium HydroxideHCID 660393-Cyclopentylpropionyl chloride

Product 1

HCID 131640443-Cyclopentylpropionitrile

Procedure

3-Cyclopentylpropionitrile is prepared in this example. 3-Cyclopentylpropionyl chloride (57.7 g, 0.36 mole) is added dropwise to a large excess of concentrated ammonium hydroxide (400 ml) cooled in an ice/salt bath. The heavy suspension of white solid is stirred overnight, collected by filtration, washed with cold water, and recrystallized from about 2 liters of boiling water. The lustrous white plates of the amide are dried in vacuo over P2O5 ; yield 31.6 g (62.3%); mp 122° C.

Workup

  1. temperaturecooled in an ice/salt bath
  2. additionThe heavy suspension of white solid
  3. filtrationcollected by filtration
  4. washwashed with cold water
  5. customrecrystallized from about 2 liters of boiling water
  6. dry with materialThe lustrous white plates of the amide are dried in vacuo over P2O5

Sources & evidence

ORD record
ord-dbe60a094eb54d9cbf931ecbfa2ec716
Source dataset
uspto-grants-1991_04
Patent number
US05008265

Reaction notes

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