N-(2,6-dimethylphenyl)formamide

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: A suspension of 125.6 g. of 2,6-dimethylformanilide in 1100 ml. of dry tetrahydrofuran is cooled to 0° C. in ice-methanol. To this with constant stirring is added dropwise over a period of 3 hours 1125 ml. of 0.96 M BH3 in tetrahydrofuran. This is then allowed to warm gradually to room temperature and then heated slowly to reflux. Refluxing is maintained for 6 hours and then stirred at room temperature another 15 hours. The reaction mixture is then cooled in ice and acidified with 425 ml. of 6 N HCl. A white solid forms. The mixture is evaporated in vacuo and the water-solid slurry dissolved into 2 l. of water. The solution is made strongly alkaline (with cooling) with 50% NaOH and then extracted twice with ether (2 l.) The ether is then washed three times with 100 ml. portions of water and twice with 100 ml. portions of saturated sodium chloride solution. The ether is then dried over sodium sulfate, filtered, acidified with ethereal HCl while cooling. The white solid which forms is filtered, washed with ether and sucked dry. This is recrystallized from isopropanol:methanol to give N,2,6-trimethylaniline hydrochloride (m.p. 255-257 dec.) A suspension of 125.6 g is added dropwise over a period of 3 hours 1125 ml heated slowly to reflux Refluxing is maintained for 6 hours stirred at room temperature another 15 hours The reaction mixture is then cooled in ice The mixture is evaporated in vacuo the water-solid slurry dissolved into 2 l (with cooling) with 50% NaOH extracted twice with ether (2 l.) The ether is then washed three times with 100 ml The ether is then dried over sodium sulfate filtered while cooling The white solid which forms is filtered washed with ether sucked dry This is recrystallized from isopropanol

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

Procedure: 125 g. of 2,6 dimethyl aniline and 375 ml. of 88% formic acid are mixed in a 1 liter bomb with magnetic stirrer. The temperature (oil bath) is brought to 120° C. The bomb is kept at this temperature for 24 hours. The bomb is then allowed to cool to room temperature and stirring continued for 48 hours. The pressure is released and the mixture is poured into an 800 ml. ice with stirring. The mixture is filtered and the solid washed extensively with water and sucked dry and then dried in vacuo at 90°-95° to give N-formyl-2,6-dimethylaniline (m.p. 163°-164.5° C.). is brought to 120° C continued for 48 hours the mixture is poured into an 800 ml ice with stirring The mixture is filtered the solid washed extensively with water sucked dry dried in vacuo at 90°-95°

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: A suspension of 125.6 g. of 2,6-dimethylformanilide in 1100 ml. of dry tetrahydrofuran is cooled to 0° C. in ice-methanol. To this with constant stirring is added dropwise over a period of 3 hours 1125 ml. of 0.96 M BH3 in tetrahydrofuran. This is then allowed to warm gradually to room temperature and then heated slowly to reflux. Refluxing is maintained for 6 hours and then stirred at room temperature another 15 hours. The reaction mixture is then cooled in ice and acidified with 425 ml. of 6 N HCl. A white solid forms. The mixture is evaporated in vacuo and the water-solid slurry dissolved into 2 l. of water. The solution is made strongly alkaline (with cooling) with 50% NaOH and then extracted twice with ether (2 l.) The ether is then washed three times with 100 ml. portions of water and twice with 100 ml. portions of saturated sodium chloride solution. The ether is then dried over sodium sulfate, filtered, acidified with ethereal HCl while cooling. The white solid which forms is filtered, washed with ether and sucked dry. This is recrystallized from isopropanol:methanol to give N,2,6-trimethylaniline hydrochloride (m.p. 255-257 dec.) A suspension of 125.6 g is added dropwise over a period of 3 hours 1125 ml heated slowly to reflux Refluxing is maintained for 6 hours stirred at room temperature another 15 hours The reaction mixture is then cooled in ice The mixture is evaporated in vacuo the water-solid slurry dissolved into 2 l (with cooling) with 50% NaOH extracted twice with ether (2 l.) The ether is then washed three times with 100 ml The ether is then dried over sodium sulfate filtered while cooling The white solid which forms is filtered washed with ether sucked dry This is recrystallized from isopropanol

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

Procedure: 125 g. of 2,6 dimethyl aniline and 375 ml. of 88% formic acid are mixed in a 1 liter bomb with magnetic stirrer. The temperature (oil bath) is brought to 120° C. The bomb is kept at this temperature for 24 hours. The bomb is then allowed to cool to room temperature and stirring continued for 48 hours. The pressure is released and the mixture is poured into an 800 ml. ice with stirring. The mixture is filtered and the solid washed extensively with water and sucked dry and then dried in vacuo at 90°-95° to give N-formyl-2,6-dimethylaniline (m.p. 163°-164.5° C.). is brought to 120° C continued for 48 hours the mixture is poured into an 800 ml ice with stirring The mixture is filtered the solid washed extensively with water sucked dry dried in vacuo at 90°-95°

Conditions: temp:100.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 4.2 0.149 g of 12, 0.112 g of 2-amino-5-fluoropyridine 4, 0.209 g of 2-(2-formyl-3-methoxyphenoxy)acetamide 3, 0.286 ml of triethylamine and, dropwise, 2.5 ml of T3P® [=propylphosphonic anhydride (50% solution in ethyl acetate)] are introduced successively into a flask with ice-cooling and under an inert gas. The reaction mixture is stirred at 100° C. for 7 h. The mixture is subsequently subjected to conventional work-up, giving 0.2 g (40%) of “A1”. cooling and under an inert gas

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

Procedure: 4.1 10.0 g of sodium acetate are dissolved in 120 ml of formic acid. 50.0 g of 2,6-dimethylaniline 11 are then introduced, and the mixture is stirred under reflux for 24 h. The mixture is subsequently subjected to conventional work-up, giving 48.9 g (79%) of N-(2,6-dimethylphenyl)formamide 12; MS-EI (M+)=149. under reflux for 24 h

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

Procedure: 4.1 10.0 g of sodium acetate are dissolved in 120 ml of formic acid. 50.0 g of 2,6-dimethylaniline 11 are then introduced, and the mixture is stirred under reflux for 24 h. The mixture is subsequently subjected to conventional work-up, giving 48.9 g (79%) of N-(2,6-dimethylphenyl)formamide 12; MS-EI (M+)=149. under reflux for 24 h

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

Procedure: A suspension of 125.6 g. of 2,6-dimethylformanilide in 1100 ml. of dry tetrahydrofuran is cooled to 0° C. in ice-methanol. To this with constant stirring is added dropwise over a period of 3 hours 1125 ml. of 0.96 M BH3 in tetrahydrofuran. This is then allowed to warm gradually to room temperature and then heated slowly to reflux. Refluxing is maintained for 6 hours and then stirred at room temperature another 15 hours. The reaction mixture is then cooled in ice and acidified with 425 ml. of 6 N HCl. A white solid forms. The mixture is evaporated in vacuo and the water-solid slurry dissolved into 2 l. of water. The solution is made strongly alkaline (with cooling) with 50% NaOH and then extracted twice with ether (2 l.) The ether is then washed three times with 100 ml. portions of water and twice with 100 ml. portions of saturation sodium chloride solution. The ether is then dried over sodium sulfate, filtered, acidified with ethereal HCl while cooling. The white solid which forms is filtered, washed with ether and sucked dry. This is recrystallized from isopropanol methanol to give N,2,6-trimethylaniline hydrochloride (m.p. 255-257 dec.) A suspension of 125.6 g is added dropwise over a period of 3 hours 1125 ml heated slowly to reflux Refluxing is maintained for 6 hours stirred at room temperature another 15 hours The reaction mixture is then cooled in ice The mixture is evaporated in vacuo the water-solid slurry dissolved into 2 l (with cooling) with 50% NaOH extracted twice with ether (2 l.) The ether is then washed three times with 100 ml The ether is then dried over sodium sulfate filtered while cooling The white solid which forms is filtered washed with ether sucked dry This is recrystallized from isopropanol methanol