Acetic Anhydride → 4-[2-(Pyridin-2-yl)ethenyl]benzonitrile

HRID 1608950Notes

Reaction equation

HRID 1608950 reaction equation
C(OC(=O)C)(=O)C.[CH3:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][N:10]=1.[C:15]([C:17]1[CH:24]=[CH:23][C:20]([CH:21]=O)=[CH:19][CH:18]=1)#[N:16]>CCOCC>[N:10]1[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=1[CH:8]=[CH:21][C:20]1[CH:23]=[CH:24][C:17]([C:15]#[N:16])=[CH:18][CH:19]=1

Participants

5

Reactant 3

HCID 7918Acetic AnhydrideHCID 79752-MethylpyridineHCID 660424-Cyanobenzaldehyde

Product 1

HCID 544767434-[2-(Pyridin-2-yl)ethenyl]benzonitrileYield 46%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A mixture of 20.4 g (0.2 mol) acetic acid anhydride, 18.6 g (0.2 mol) 2-methylpyridine and 26.2 g (0.2 mol) 4-cyanobenzaldehyde is heated to reflux for 24 h. One allows to cool, mixes with excess ether and filters. One isolates 18.8 g of title compound (46% of theory) of the m.p. 98°-98° C.

Workup

  1. temperatureis heated
  2. temperatureto reflux for 24 h
  3. temperatureto cool

Sources & evidence

ORD record
ord-af7dd83a9f78453fbf7a21fd7f3a6ed5
Source dataset
uspto-grants-1995_03
Patent number
US05399575

Reaction notes

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