4-Fluoroaniline → HCID 70255947, compound

Reaction equation

[F:1][C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[CH:4][CH:3]=1.O=[C:10]1[CH2:14][CH2:13][CH2:12][CH:11]1[C:15]#[N:16].[Cl-].[Ca+2].[Cl-]>>[F:1][C:2]1[CH:8]=[CH:7][C:5]([NH:6][C:10]2[CH2:14][CH2:13][CH2:12][C:11]=2[C:15]#[N:16])=[CH:4][CH:3]=1

Participants

Reactant 3

HCID 97314-Fluoroaniline

HCID 989302-Oxocyclopentane-1-carbonitrile

HCID 5284359Calcium Chloride

Product 1

HCID 70255947HCID 70255947, compound

Procedure

4-Fluoro-aniline (Aldrich Chemicals) (2.3 g, 21 mmol), cyano-ketone (Example 11) (2.2 g, 20 mmol), calcium chloride (2.5 g, 23 mmol) and T.H.F. (30 ml) were heated under reflux for 21 hours. After being allowed to cool, the mixture was filtered and the solvent evaporated. Kugelrohr distillation (160° C., 0.4 mm Hg) gave the product as an off-white powder.