2-oxocyclopentane-1-carbonitrile

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 3,5-Difluoro-aniline (Aldrich Chemicals) (2.6 g, 20.0 mmol), 2-oxocyclopentane carbonitrile (Example 11) (2.2 g, 20.2 mmol), calcium chloride (2.5 g, 22.5 mmol) and T.H.F. were heated under reflux for 24 hours. After cooling the mixture was filtered and the solvent evaporated. Kugelrohr distillation (140° C., 0.3 mmHg) gave the product as pale yellow crystals. were heated under reflux for 24 hours After cooling the mixture was filtered the solvent evaporated Kugelrohr distillation (140° C., 0.3 mmHg)

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 2,5-Difluoro-aniline (2.6 g, 20.0 mmol) (Aldrich Chemicals) cyano-ketone (Example 11) (2.2 g, 20.2 mmol), calcium chloride (2.5 g, 22.5 mmol) and T.H.F. (30 ml) were heated under reflux for 22 hours. After cooling, the mixture was filtered and the solvent evaporated. Kugelrohr distillation (160° C., 0.9 mmHg) gave the produce as white crystals. (30 ml) were heated under reflux for 22 hours After cooling the mixture was filtered the solvent evaporated Kugelrohr distillation (160° C., 0.9 mmHg) gave the produce as white crystals

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 2,4-Difluoro-aniline (2.6 g, 20.0 mmol) (Aldrich Chemicals) cyano-ketone (Example 11) (2.2 g, 20.2 mmol), calcium chloride (2.5 g, 22.5 mmol) and T.H.F. (30 ml) were heated under reflux for 19 hours. After cooling, the mixture was filtered and the solvent evaporated. Kugelrohr distillation (125° C., 0.25 mmHg) gave the product as pale yellow crystals. (30 ml) were heated under reflux for 19 hours After cooling the mixture was filtered the solvent evaporated Kugelrohr distillation (125° C., 0.25 mmHg)

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 3-Chloro-aniline (Aldrich Chemicals) (5.1 g, 40.0 mmol), cyano-ketone (Example 11) (4.4 g, 40.4 mmol) and calcium chloride (5.0 g, 45.0 mmol) in T.H.F. (60 ml) were heated under reflux for 17 hours. After cooling, the mixture was filtered and the solvent evaporated. Kugelrohr distillation (150° C., 0.2 mmHg) gave the product as light yellow powder. (60 ml) were heated under reflux for 17 hours After cooling the mixture was filtered the solvent evaporated Kugelrohr distillation (150° C., 0.2 mmHg)

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 4-Bromo-aniline (Aldrich Chemicals) (3.5 g, 20 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 7 hours. After being allowed to cool, the mixture was filtered and the solvent evaporated. Kugelrohr distillation (150° C., 0.07 mmHg) gave the product as a brown-grey powder. (30 ml) were heated under reflux for 7 hours to cool the mixture was filtered the solvent evaporated Kugelrohr distillation (150° C., 0.07 mmHg)

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

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. (30 ml) were heated under reflux for 21 hours to cool the mixture was filtered the solvent evaporated Kugelrohr distillation (160° C., 0.4 mm Hg)

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 3-Fluoro-aniline (Aldrich Chemicals) (4.6 g, 41 mmol), cyano-ketone (Example 11) (4.4 g, 40 mmol), calcium chloride (5.0 g, 45 mmol) and T.H.F. (60 ml) were heated under reflux for 17 hours. After being allowed to cool, the mixture was filtered and the solvent evaporated. Kugelrohr distillation (125° C., 0.02 mm Hg) gave the product as a pale yellow powder. (60 ml) were heated under reflux for 17 hours to cool the mixture was filtered the solvent evaporated Kugelrohr distillation (125° C., 0.02 mm Hg)

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 2-Fluoro-aniline (Aldrich Chemicals) (2.3 g, 21 mmol), cyanoketone (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 24 hours. After being allowed to cool, the mixture was filtered and the solvent evaporated. Kugelrohr distillation (125° C. 0.05 mm Hg) have the product as an off-white power. (30 ml) were heated under reflux for 24 hours to cool the mixture was filtered the solvent evaporated Kugelrohr distillation (125° C. 0.05 mm Hg)

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 4-Chloro-aniline (Aldrich Chemicals) (2.6 g, 20 mmol), cyanoketone (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 19 hours. After being allowed to cool, the mixture was filtered and the solvent evaporated. Kugelrohr distillation (160° C., 0.3 mm Hg) gave the product as white crystals. (30 ml) were heated under reflux for 19 hours to cool the mixture was filtered the solvent evaporated Kugelrohr distillation (160° C., 0.3 mm Hg)

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 3,5-Difluoro-aniline (Aldrich Chemicals) (2.6 g, 20.0 mmol), 2-oxocyclopentane carbonitrile (Example 11) (2.2 g, 20.2 mmol), calcium chloride (2.5 g, 22.5 mmol) and T.H.F. were heated under reflux for 24 hours. After cooling the mixture was filtered and the solvent evaporated. Kugelrohr distillation (140° C., 0.3 mmHg) gave the product as pale yellow crystals. were heated under reflux for 24 hours After cooling the mixture was filtered the solvent evaporated Kugelrohr distillation (140° C., 0.3 mmHg)

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 2,5-Difluoro-aniline (2.6 g, 20.0 mmol) (Aldrich Chemicals) cyano-ketone (Example 11) (2.2 g, 20.2 mmol), calcium chloride (2.5 g, 22.5 mmol) and T.H.F. (30 ml) were heated under reflux for 22 hours. After cooling, the mixture was filtered and the solvent evaporated. Kugelrohr distillation (160° C., 0.9 mmHg) gave the produce as white crystals. (30 ml) were heated under reflux for 22 hours After cooling the mixture was filtered the solvent evaporated Kugelrohr distillation (160° C., 0.9 mmHg) gave the produce as white crystals