2-(2-methoxyphenyl)acetonitrile

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

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

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

Procedure: Corresponding to J. Org. Chem. 40 (1975) 3497, 16.7 g of 2-methoxyphenylacetonitrile, 158 ml of lithium triisopropyl-amide (2 mol solution) and 46.7 ml of 1,2-dichloroethane in 96 ml of tetrahydrofuran and 58.6 ml of hexamethylphosphoric acid triamide are reacted with one another. 5.6 g of 1-(2-methoxy-phenyl)-cyclopropyl-carbonitrile, boiling point 104-115° C./0.1 mbar, which was also reacted as described for 3-(1-phenyl-cyclobutyl)-2-oxo-propionic acid, is obtained. 3-[1-(2-Methoxyphenyl)-cyclopropyl]-2-oxo-propionic acid is thus obtained as an oil. is obtained

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

Procedure: To a slurry of sodium hydride (3.39 g of 60% in mineral oil, 84.9 mmol) in tetrahydrofuran (200 mL) at room temperature was added 2-(2-methoxyphenyl)acetonitrile (10.0 g, 67.9 mmol) dropwise. The reaction mixture was then heated to reflux and the gray suspension turned dark red over 30 min. Diphenyl carbonate (18.2 g, 84.9 mmol) was added portionwise, and the reaction suspension was heated at reflux for an additional 18 h. The reaction mixture was cooled, poured into 1 N HCl (200 mL) and extracted with ethyl acetate (3×200 mL). The organic phases were combined, dried over magnesium sulfate, filtered and concentrated onto Celite® under reduced pressure. The resultant residue was purified by chromatography on silica gel using 10-90% ethyl acetate/hexane as eluant to give the title compound as a light yellow solid (14.3 g). The reaction mixture was then heated to reflux the reaction suspension was heated at reflux for an additional 18 h The reaction mixture was cooled extracted with ethyl acetate (3×200 mL) dried over magnesium sulfate filtered concentrated onto Celite® under reduced pressure The resultant residue was purified by chromatography on silica gel using 10-90% ethyl acetate/hexane as eluant

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

Procedure: The title compound was prepared according to Example 1, starting from 2-methoxybenzyl cyanide and 2,4 -diamino-5-pyrimidine-carboxaldehyde; mp 304-306° C. (dec).

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

Procedure: According to the procedure described by Example 1, o-methoxybenzylcyanide (18.6 g, 127 mmol) is condensed with acetone (50 ml) under addition of methanol (6.5 ml) and KOH (3.33 g, 50 mmol) to yield, after workup and distillation at 106-110° C./0.05 mbar, 2-(2-methoxyphenyl)-3-methyl-but-2-ene nitrile (1.7 g, 7%). to yield after workup and distillation at 106-110° C./0.05 mbar, 2-(2-methoxyphenyl)-3-methyl-but-2-ene nitrile (1.7 g, 7%)

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

Procedure: By a method analogous to that of Example 3(a), o-methoxybenzyl cyanide was methylated with methyl iodide and sodium hydride in dimethylformamide to give the desired compound in 85% yield.

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

Procedure: A mixture of (2-methoxyphenyl)acetonitrile (147 g and 1,2-dibromomethane (168 ml) in dimethylsulphoxide (250 ml) was added over 1 hour to a stirred suspension of powdered potassium hydroxide (250 g) and 18-Crown-6 (5 g) in dimethylsulphoxide (1200 ml) at 25° C. Stirring was continued for 20 hours. Water (1200 ml) was added and the mixture extracted with ether to give a crude oil which was purified by distillation (b.p. 102°/0.25) to give 1-(2-methoxyphenyl)cyclopropane carbonitrile. the mixture extracted with ether to give a crude oil which was purified by distillation (b.p. 102°/0.25)

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

Procedure: Corresponding to J. Org. Chem. 40 (1975) 3497, 16.7 g of 2-methoxyphenylacetonitrile, 158 ml of lithium triisopropylamide (2 molar solution) and 46.7 ml of 1,2-dichloroethane in 96 ml of tetrahydrofuran and 58.6 ml of hexamethylphosphoric acid triamide are reacted with one another. 5.6 g of 1-(2-methoxyphenyl)-cyclopropyl-carbonitrile, boiling point 104-115° C. (0.1 mbar), which is further reacted as described for 3-(1-phenyl-cyclobutyl)-2-oxo-propionic acid, is obtained. 3-[1-(2-Methoxyphenyl)-cyclopropyl]-2-oxo-propionic acid is thus obtained as an oil. is obtained

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

Procedure: Into a 500 mL round-bottomed flask was added 2-(2-methoxyphenyl)acetonitrile (50.45 g, 343 mmol) in ethanol (101 mL). HCl (10.42 mL, 343 mmol) gas was bubbled through the suspension for 15 minutes. The HCl bubbler was removed and the reaction was stirred at ambient temperature for 48 hours. The reaction was diluted with 200 mL ether, and the suspension was filtered. The collected solid was washed with ether and dried under vacuum to provide the title compound as the hydrochloride salt. MS (DCI+) m/e 194.0 (M+H)+. The HCl bubbler was removed The reaction was diluted with 200 mL ether the suspension was filtered The collected solid was washed with ether dried under vacuum

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

Procedure: The title compound was prepared according to Example 1, starting from 2-methoxybenzyl cyanide and 2,4-diamino-5-pyrimidine-carboxaldehyde; mp 304°-306° C. (dec).

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