2-hex-1-ynylaniline

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

Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A solution of 2 g of sodium nitrite in 60 ml of water was added at 0° C. to a suspension at 0° C. of 3.2 g of the product of Step A in 100 ml of concentrated hydrochloric acid, and the mixture was stirred for 90 minutes at 0° C., then for one hour at 100° C. The reaction medium was poured into 100 ml of ice-cooled water, separated and washed with ice-cooled water. The moist product was taken up in 100 ml of water and alkalized with concentrated ammonium hydroxide. After separation, the residue was washed with water and dried at 70° C. under reduced pressure to obtain 1.47 g of the expected product melting at 180° C. for one hour at 100° C separated washed with ice- cooled water After separation the residue was washed with water dried at 70° C. under reduced pressure

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

Procedure: 32 mg of copper iodide and 140 mg of bistriphenyl phosphine palladium chloride and 2.3 ml of 1-hexyne were added to a solution of 4.4 g of 2-iodo aniline in 100 ml of triethylamine and the mixture was stirred for 15 hours at ambient temperature, then evaporated to dryness. The residue was taken up in ether and the insoluble part was filtered out, washed with ether and the ethereal fractions were evaporated to dryness. The residue was chromatographed on silica (eluant:hexane-ethyl acetate (9-1)) to obtain 3.27 of the desired product. evaporated to dryness the insoluble part was filtered out washed with ether the ethereal fractions were evaporated to dryness The residue was chromatographed on silica (eluant:hexane-ethyl acetate (9-1))

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

Procedure: 32 mg of copper iodide and 140 mg of bistriphenyl phosphine palladium choride and 2.3 of 1-hexyne were added to a solution of 4.4 g of 2-iodo aniline in 100 ml of triethylamine and the mixture was stirred for 15 hours at ambient temperature, then evaporated to dryness. The residue was taken up in ether and the insoluble part was filtered out, wash with ether and the ethereal fractions were evaporated to dryness. The residue was chromatographed on silica (eluant: hexane-ethyl acetate (9-1)) to obtain 3.27 g of the desired product. evaporated to dryness the insoluble part was filtered out wash with ether the ethereal fractions were evaporated to dryness The residue was chromatographed on silica (eluant: hexane-ethyl acetate (9-1))

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

Procedure: 32 mg of copper iodide and 140 mg of bistriphenyl phosphine palladium choride and 2.3 of 1-hexyne were added to a solution of 4.4 g of 2-iodo aniline in 100 ml of triethylamine and the mixture was stirred for 15 hours at ambient temperature, then evaporated to dryness. The residue was taken up in ether and the insoluble part was filtered out, wash with ether and the ethereal fractions were evaporated to dryness. The residue was chromatographed on silica (eluant: hexane-ethyl acetate (9-1)) to obtain 3.27 g of the desired product. evaporated to dryness the insoluble part was filtered out wash with ether the ethereal fractions were evaporated to dryness The residue was chromatographed on silica (eluant: hexane-ethyl acetate (9-1))

Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A solution of 2 g of sodium nitrite in 60 ml of water was added at 0° C. to a suspension at 0° C. of 3.2 g of the product of Step A in 100 ml of concentrated hydrochloric acid, and the mixture was stirred for 90 minutes at 0° C., then for one hour at 100° C. The reaction medium was poured into 100 ml of ice-cooled water, separated and washed with ice-cooled water. The moist product was taken up in 100 ml of water and alkalized with concentrated ammonium hydroxide. After separation, the residue was washed with water and dried at 70° C. under reduced pressure to obtain 1.47 g of the expected product melting at 180° C. for one hour at 100° C separated washed with ice- cooled water After separation the residue was washed with water dried at 70° C. under reduced pressure

Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A solution of 2 g of sodium nitrite in 60 ml of water was added at 0° C. to a suspension at 0° C. of 3.2 g of the product of Step A in 100 ml of concentrated hydrochloric acid, and the mixture was stirred for 90 minutes at 0° C., then for one hour at 100° C. The reaction medium was poured into 100 ml of ice-cooled water, separated and washed with ice-cooled water. The moist product was taken up in 100 ml of water and alkalized with concentrated ammonium hydroxide. After separation, the residue was washed with water and dried at 70° C. under reduced pressure to obtain 1.47 g of the expected product melting at 180° C. for one hour at 100° C separated washed with ice- cooled water After separation the residue was washed with water dried at 70° C. under reduced pressure

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

Procedure: 32 mg of copper iodide and 140 mg of bistriphenyl phosphine palladium chloride and 2.3 ml of 1-hexyne were added to a solution of 4.4 g of 2-iodo aniline in 100 ml of triethylamine and the mixture was stirred for 15 hours at ambient temperature, then evaporated to dryness. The residue was taken up in ether and the insoluble part was filtered out, washed with ether and the ethereal fractions were evaporated to dryness. The residue was chromatographed on silica (eluant:hexane-ethyl acetate (9-1)) to obtain 3.27 of the desired product. evaporated to dryness the insoluble part was filtered out washed with ether the ethereal fractions were evaporated to dryness The residue was chromatographed on silica (eluant:hexane-ethyl acetate (9-1))

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

Procedure: 32 mg of copper iodide and 140 mg of bistriphenyl phosphine palladium chloride and 2.3 ml of 1-hexyne were added to a solution of 4.4 g of 2-iodo aniline in 100 ml of triethylamine and the mixture was stirred for 15 hours at ambient temperature, then evaporated to dryness. The residue was taken up in ether and the insoluble part was filtered out, washed with ether and the ethereal fractions were evaporated to dryness. The residue was chromatographed on silica (eluant:hexane-ethyl acetate (9-1)) to obtain 3.27 of the desired product. evaporated to dryness the insoluble part was filtered out washed with ether the ethereal fractions were evaporated to dryness The residue was chromatographed on silica (eluant:hexane-ethyl acetate (9-1))

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

Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A solution of 2 g of sodium nitrate in 60 ml of water was added at 0° C. to a suspension at 0° C. of 3.2 g of the product of Step A in 100 ml of concentrated hydrochloric acid. The mixture was stirred for 90 minutes at 0° C., then for one hour at 100° C. The reaction medium was poured into 100 ml of ice-cooled water, followed by separating and washing with ice-cooled water. The moist product was taken up in 100 ml of water and alkalized with concentrated ammonium hydroxide. After separating, the residue was washed with water and dried at 70° C. under reduced pressure to obtain 1.47 g of the expected product melting at 180° C. for one hour at 100° C by separating washing with ice- cooled water After separating the residue was washed with water dried at 70° C. under reduced pressure

Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A solution of 2 g of sodium nitrate in 60 ml of water was added at 0° C. to a suspension at 0° C. of 3.2 g of the product of Step A in 100 ml of concentrated hydrochloric acid. The mixture was stirred for 90 minutes at 0° C., then for one hour at 100° C. The reaction medium was poured into 100 ml of ice-cooled water, followed by separating and washing with ice-cooled water. The moist product was taken up in 100 ml of water and alkalized with concentrated ammonium hydroxide. After separating, the residue was washed with water and dried at 70° C. under reduced pressure to obtain 1.47 g of the expected product melting at 180° C. for one hour at 100° C by separating washing with ice- cooled water After separating the residue was washed with water dried at 70° C. under reduced pressure