5-Bromopentanenitrile → HCID 54178215, compound

HRID 1608949Notes

Reaction equation

HRID 1608949 reaction equation
[Na].[N:2]1[CH:7]=[CH:6][C:5]([CH:8]=[CH:9][C:10]2[CH:15]=[CH:14][C:13]([OH:16])=[CH:12][CH:11]=2)=[CH:4][CH:3]=1.Br[CH2:18][CH2:19][CH2:20][CH2:21][C:22]#[N:23]>CC(O)C>[N:2]1[CH:7]=[CH:6][C:5]([CH:8]=[CH:9][C:10]2[CH:11]=[CH:12][C:13]([O:16][CH2:18][CH2:19][CH2:20][CH2:21][C:22]#[N:23])=[CH:14][CH:15]=2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 794355-BromopentanenitrileHCID 682482HCID 682482, compoundHCID 5360545Sodium

Product 1

HCID 54178215HCID 54178215, compoundYield 86%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

To the solution of 1.16 g (50 mmol) sodium in 250 ml 2-propanol one adds 10.0 g (50 mmol) 4-[2-(4-pyridinyl)-ethenyl]-phenol, heats under reflux for 10 min, allows to cool, adds thereto 8.1 g (50 mmol) 5-bromovaleronitrile and heats to reflux for 16 h. One evaporates, mixes with water, extracts with dichloromethane, dries the extract, evaporates and triturates the residue with ether. One obtains 11.9 g of title compound (86% of theory) of the m.p. 85°-87° C.

Workup

  1. temperatureunder reflux for 10 min
  2. temperatureto cool
  3. additionadds
  4. temperatureto reflux for 16 h
  5. customOne evaporates
  6. customevaporates

Sources & evidence

ORD record
ord-387307b64eba42bd8446465d9a763f90
Source dataset
uspto-grants-1995_03
Patent number
US05399575

Reaction notes

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