Sodium Hydroxide → [2,4'-Bipyridine]-5-carbonitrile

HRID 1594385Notes

Reaction equation

HRID 1594385 reaction equation
Br[C:2]1[CH:3]=[CH:4][C:5]([C:8]2[CH:13]=[CH:12][N:11]=[CH:10][CH:9]=2)=[N:6][CH:7]=1.[Cu][C:15]#[N:16].[OH-].[Na+]>CN(C)C(=O)C>[C:15]([C:2]1[CH:3]=[CH:4][C:5]([C:8]2[CH:13]=[CH:12][N:11]=[CH:10][CH:9]=2)=[N:6][CH:7]=1)#[N:16]

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 116587125-Bromo-2,4'-bipyridineHCID 178418546HCID 178418546, compound

Product 1

HCID 11355854[2,4'-Bipyridine]-5-carbonitrileYield 83%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

By the same method as in Example 1,5-bromo-2,4′-bipyridine was prepared. The resulting 5-bromo-2,4′-bipyridine (7.0 g) was dissolved in N,N-dimethylacetamide (15 ml), followed by addition of copper (I) cyanide (2.8 g), for agitation at 140° C. for 3 hours. After the reaction solution was cooled, aqueous 25% NaOH solution (10 ml) was added to deposit a crystal, which was filtered and recovered, to obtain the object substance (4.5 g; yield of 83%).

Workup

  1. temperatureAfter the reaction solution was cooled
  2. filtrationwas filtered
  3. customrecovered
  4. customto obtain the object substance (4.5 g; yield of 83%)

Sources & evidence

ORD record
ord-f1b70f946cef43fab9b9e3e3316e0bf5
Source dataset
uspto-grants-2007_11
Patent number
US07301029B2

Reaction notes

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