4'-Cyanoacetophenone → 4-[3-(3-Cyanophenyl)-1-oxo-2-propenyl]benzonitrile

HRID 1586229Notes

Reaction equation

[C:1]([C:3]1[CH:4]=[C:5]([CH:8]=[CH:9][CH:10]=1)[CH:6]=O)#[N:2].[C:11]([C:14]1[CH:21]=[CH:20][C:17]([C:18]#[N:19])=[CH:16][CH:15]=1)(=[O:13])[CH3:12]>>[C:1]([C:3]1[CH:4]=[C:5]([CH:6]=[CH:12][C:11]([C:14]2[CH:21]=[CH:20][C:17]([C:18]#[N:19])=[CH:16][CH:15]=2)=[O:13])[CH:8]=[CH:9][CH:10]=1)#[N:2]

Participants

Reactant 2

HCID 740444'-Cyanoacetophenone

HCID 90670m-Formylbenzonitrile

Product 1

HCID 544991854-[3-(3-Cyanophenyl)-1-oxo-2-propenyl]benzonitrile

Procedure

Part A. Employing methods similar to Example 1 Part A but using m-cyano benzaldehyde (0.91 gm, 6.89 mmol) and 4-acetyl benzonitrile (1.0 gm, 6.89 mmol), 4-[3-(3-cyanophenyl)-1-oxo-2-propenyl]benzonitrile was isolated as a pale yellow powder, 1.4 gm (79%), 1H NMR (CDCl3) 8.53(s,1H), 8.35(d,2H), 8.15-8.20(m,3H), 7.92(d, 1H), 7.82(d, 1H), 7.67(t, 1H).

Sources & evidence

ORD record: ord-e52ee0274e43411596cc5cd44fb963d3
Source dataset: uspto-grants-1999_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05942544

Reaction notes

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