2-[2-(cyanomethyl)phenyl]acetonitrile

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

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

Procedure: 1,2-Phenylenediacetonitrile (7.5 g, 48 mmol) dissolved in ethanol (150 ml) was added to Raney Ni (2 g) which had been previously washed with ethanol (3×20 ml). The mixture was then hydrogenated at 50° C. at 50 psi pressure with shaking for 24 h. The reaction mixture was then cooled to room temperature and filtered through a pad of kieselguhr and washed through with ethanol (100 ml). The filtrate was evaporated in vacuo to give a brown oil which was chromatographed on silica gel (100 g), eluting with 2-10% methanol in CH2Cl2 to give the title compound as a brown oil (2.45 g, 35%). had been previously washed with ethanol (3×20 ml) was then hydrogenated at 50° C. at 50 psi pressure filtered through a pad of kieselguhr washed through with ethanol (100 ml) The filtrate was evaporated in vacuo to give a brown oil which was chromatographed on silica gel (100 g) eluting with 2-10% methanol in CH2Cl2

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

Procedure: 1,2-phenylenediacetonitrile (1.0 g, 6.40 mmol) was dissolved in 5 ml ethyl alcohol and 2 ml concentrated sulfuric acid in a 25 ml round bottom flask. The mixture was stirred and heated to reflux for 6 hours. After neutralizing the reaction solution with ammonium hydroxide, the result solution was extracted with ethyl acetate (3×50 ml). The organic phase was combined and dried with Na2SO4. Concentration of the ethyl acetate afforded a yellow liquid. Running column with hexane: acetyl acetate=10:1, got yellow liquid 1.13 g (70.6%). 1H NMR (DMSO-d6): δ 1.24(t, 6H, CH3), δ 3.7 (s, 4H, CH2CO), δ 4.16(q, 4H, OCH2), δ 7.3 (d, 4H, Ar—H). heated to reflux for 6 hours the result solution was extracted with ethyl acetate (3×50 ml) dried with Na2SO4 Concentration of the ethyl acetate afforded a yellow liquid

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

Procedure: The naphtholactam compounds of the formula (II) used as starting products are obtainable by reacting o-xylylenedicyanide with glyoxal in the presence of a base (NaOH, KOH) and of a solvent at temperatures below 50° C. (e.g. 0° to 40° C.) to give 1,4-dicyanonaphthalene, and subsequently either

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

Procedure: 1,2-Phenylenediacetonitrile (7.5 g, 48 mmol) dissolved in ethanol (150 ml) was added to Raney Ni (2 g) which had been previously washed with ethanol (3×20 ml). The mixture was then hydrogenated at 50° C. at 50 psi pressure with shaking for 24 h. The reaction mixture was then cooled to room temperature and filtered through a pad of kieselguhr and washed through with ethanol (100 ml). The filtrate was evaporated in vacuo to give a brown oil which was chromatographed on silica gel (100 g), eluting with 2-10% methanol in CH2Cl2 to give the title compound as a brown oil (2.45 g, 35%). had been previously washed with ethanol (3×20 ml) was then hydrogenated at 50° C. at 50 psi pressure filtered through a pad of kieselguhr washed through with ethanol (100 ml) The filtrate was evaporated in vacuo to give a brown oil which was chromatographed on silica gel (100 g) eluting with 2-10% methanol in CH2Cl2

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

Procedure: 1,2-Phenylenediacetonitrile (7.5 g, 48 mmol) dissolved in ethanol (150 ml) was added to Raney Ni (2 g) which had been previously washed with ethanol (3×20 ml). The mixture was then hydrogenated at 50° C. at 50 psi pressure with shaking for 24 h. The reaction mixture was then cooled to room temperature and filtered through a pad of kieselguhr and washed through with ethanol (100 ml). The filtrate was evaporated in vacuo to give a brown oil which was chromatographed on silica gel (100 g), eluting with 2-10% methanol in CH2Cl2 to give the title compound as a brown oil (2.45 g, 35%). had been previously washed with ethanol (3×20 ml) was then hydrogenated at 50° C. at 50 psi pressure filtered through a pad of kieselguhr washed through with ethanol (100 ml) The filtrate was evaporated in vacuo to give a brown oil which was chromatographed on silica gel (100 g) eluting with 2-10% methanol in CH2Cl2

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

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

Procedure: 1,2-Phenylenediacetonitrile (7.5 g, 48 mmol) dissolved in ethanol (150 ml) was added to Raney Ni (2 g) which had been previously washed with ethanol (3×20 ml). The mixture was then hydrogenated at 50° C. at 50 psi pressure with shaking for 24 h. The reaction mixture was then cooled to room temperature and filtered through a pad of kieselguhr and washed through with ethanol (100 ml). The filtrate was evaporated in vacuo to give a brown oil which was chromatographed on silica gel (100 g), eluting with 2-10% methanol in CH2Cl2 to give the title compound as a brown oil (2.45 g, 35%). had been previously washed with ethanol (3×20 ml) was then hydrogenated at 50° C. at 50 psi pressure filtered through a pad of kieselguhr washed through with ethanol (100 ml) The filtrate was evaporated in vacuo to give a brown oil which was chromatographed on silica gel (100 g) eluting with 2-10% methanol in CH2Cl2

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

Procedure: 1,2-phenylenediacetonitrile (1.0 g, 6.40 mmol) was dissolved in 5 ml ethyl alcohol and 2 ml concentrated sulfuric acid in a 25 ml round bottom flask. The mixture was stirred and heated to reflux for 6 hours. After neutralizing the reaction solution with ammonium hydroxide, the result solution was extracted with ethyl acetate (3×50 ml). The organic phase was combined and dried with Na2SO4. Concentration of the ethyl acetate afforded a yellow liquid. Running column with hexane: acetyl acetate=10:1, got yellow liquid 1.13 g (70.6%). 1H NMR (DMSO-d6): δ 1.24 (t, 6H, CH3), δ 3.7 (s, 4H, CH2CO), δ 4.16 (q, 4H, OCH2), δ 7.3 (d, 4H, Ar—H). heated to reflux for 6 hours the result solution was extracted with ethyl acetate (3×50 ml) dried with Na2SO4 Concentration of the ethyl acetate afforded a yellow liquid

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

Procedure: 1,2-phenylenediacetonitrile (1.0 g, 6.40 mmol) was dissolved in 5 ml ethyl alcohol and 2 ml concentrated sulfuric acid in a 25 ml round bottom flask. The mixture was stirred and heated to reflux for 6 hours. After neutralizing the reaction solution with ammonium hydroxide, the result solution was extracted with ethyl acetate (3×50 ml). The organic phase was combined and dried with Na2SO4. Concentration of the ethyl acetate afforded a yellow liquid. Running column with hexane: acetyl acetate=10:1, got yellow liquid 1.13 g (70.6%). 1H NMR (DMSO-d6): δ 1.24 (t, 6H, CH3), δ 3.7 (s, 4H, CH2CO), δ 4.16 (q, 4H, OCH2), δ 7.3 (d, 4H, Ar—H). heated to reflux for 6 hours the result solution was extracted with ethyl acetate (3×50 ml) dried with Na2SO4 Concentration of the ethyl acetate afforded a yellow liquid

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

Procedure: 1,2-phenylenediacetonitrile (1.0 g, 6.40 mmol) was dissolved in 5 ml ethyl alcohol and 2 ml concentrated sulfuric acid in a 25 ml round bottom flask. The mixture was stirred and heated to reflux for 6 hours. After neutralizing the reaction solution with ammonium hydroxide, the result solution was extracted with ethyl acetate (3×50 ml). The organic phase was combined and dried with Na2SO4. Concentration of the ethyl acetate afforded a yellow liquid. Running column with hexane: acetyl acetate=10:1, got yellow liquid 1.13 g (70.6%). 1H NMR (DMSO-d6): δ 1.24 (t, 6H, CH3), δ 3.7 (s, 4H, CH2CO), δ 4.16 (q, 4H, OCH2), δ 7.3 (d, 4H, Ar—H). heated to reflux for 6 hours the result solution was extracted with ethyl acetate (3×50 ml) dried with Na2SO4 Concentration of the ethyl acetate afforded a yellow liquid

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

Procedure: 1,2-phenylenediacetonitrile (1.0 g, 6.40 mmol) was dissolved in 5 ml ethyl alcohol and 2 ml concentrated sulfuric acid in a 25 ml round bottom flask. The mixture was stirred and heated to reflux for 6 hours. After neutralizing the reaction solution with ammonium hydroxide, the result solution was extracted with ethyl acetate (3×50 ml). The organic phase was combined and dried with Na2SO4. Concentration of the ethyl acetate afforded a yellow liquid. Running column with hexane: acetyl acetate=10:1, got yellow liquid 1.13 g (70.6%). 1H NMR (DMSO-d6): δ 1.24(t, 6H, CH3), δ 3.7 (s, 4H, CH2CO), δ 4.16(q, 4H, OCH2), δ 7.3 (d, 4H, Ar—H). heated to reflux for 6 hours the result solution was extracted with ethyl acetate (3×50 ml) dried with Na2SO4 Concentration of the ethyl acetate afforded a yellow liquid