2-methylbut-2-enenitrile

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

Procedure: A mixture of approximately 70 weight percent cis-2-pentenenitrile, 14 weight percent 2-methyl-2-butenenitrile, 4 weight percent 2-methyl-3-butenenitrile, with cyclohexane, benzene, and valeronitrile making up the balance, was reacted with 29 weight percent aqueous ammonia (at 15 percent molar excess relative to cis-2-pentenenitrile) in a stirred batch reactor at about 90° to 100° C., at an autogeneous pressure of about 60 to 118 psig, for approximately ten hours Vacuum distillation of the crude reaction mixture to remove low boiling impurities and water resulted in 91% selectivity to 3-aminopentanenitrile at 97% conversion of the starting cis-2-pentenenitrile Vacuum distillation of the crude reaction mixture to remove low boiling impurities and water

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

Procedure: Into a 500 ml 4-neck flask, equipped with a stirrer, reflux cooler, dropping funnel and water separator, 126.5 g (1 mole) of benzylchloride, 81 g (1 mole) of 2-methyl-2-butene-nitrile, 100 ml of toluene, and 10 g of tetrabutylammonium bromide were first introduced and heated to reflux. To this mixture, 40 g (1 mole) of solid sodium hyroxide were added in portions. The reaction mixture was then maintained one more hour at reflux. Thereupon, it was washed to neutrality with water, the phases were separated and the organic phase distilled as described in Example 1. The yield in desired product was 103.5 g, corresponding to 61% of the theoretical. Into a 500 ml 4-neck flask, equipped with a stirrer reflux cooler heated to reflux The reaction mixture was then maintained one more hour at reflux Thereupon, it was washed the phases were separated the organic phase distilled

Conditions: temp:70.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Into a 1 liter 4-neck flask equipped with a stirrer, reflux cooler, and dropping funnel, 48 g (1.2 moles) of solid sodium hydroxide, 200 ml of toluene and 10 g of tetrabutyl ammonium bromide were first introduced, and heated to 70° C. Within 2 hours, a mixture of 81 g (1 mole) of 2-methyl-2-butenenitrile, and 125.4 g (1.2 moles) of prenyl chloride were added dropwise while stirring. Thereupon, the reaction mixture was further stirred for 3 hours at 75° C. For processing the reaction mixture, excess sodium hydroxide and sodium chloride formed in the reaction were first washed out with water. Then the phases were separated, and the organic phase washed with water to neutrality. After withdrawing the solvent, distillation took place in vacuo in a 30 cm. Vigreux column. The yield in desired product amounted to 62 g, ; corresponding to 41% of the theoretical. Into a 1 liter 4-neck flask equipped with a stirrer reflux cooler were added dropwise Thereupon, the reaction mixture was further stirred for 3 hours at 75° C formed in the reaction were first washed out with water Then the phases were separated the organic phase washed with water to neutrality After withdrawing the solvent, distillation

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

Procedure: A mixture of approximately 70 weight percent cis-2-pentenenitrile, 14 weight percent 2-methyl-2-butenenitrile, 4 weight percent 2-methyl-3-butenenitrile, with cyclohexane, benzene, and valeronitrile making up the balance, was reacted with 29 weight percent aqueous ammonia (at 15 percent molar excess relative to cis-2-pentenenitrile) in a stirred batch reactor at about 90° to 100° C., at an autogeneous pressure of about 60 to 118 psig, for approximately ten hours Vacuum distillation of the crude reaction mixture to remove low boiling impurities and water resulted in 91% selectivity to 3-aminopentanenitrile at 97% conversion of the starting cis-2-pentenenitrile Vacuum distillation of the crude reaction mixture to remove low boiling impurities and water