N-phenylpentanamide

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

Procedure: To a solution of 2-n-propylaniline (8.91 g, 66 mmol) and Et3N (14 mL, 106 mmol) in CH2Cl2 (60 mL) was added acetic anhydride (10.9 mL, 99 mmol) dropwise. The resulting mixture was allowed to stir at room temp. overnight, then was treated with a 1N HCl solution (40 mL). The acidic mixture was extracted with CH2Cl2 (2×30 mL). The combined organic layers were sequentially washed with H2O (40 mL), a 1N NaOH solution (40 mL), H2O (40 mL) and a saturated NaCl solution (40 mL), dried (Na2SO4), and concentrated under reduced pressure. The resulting powder was purified by crystalization (EtOAc) to give 2-n-propylacetanilide as white needles (7.85 g, 67%). TLC (30% EtOAc/hex) Rf0.37. The acidic mixture was extracted with CH2Cl2 (2×30 mL) The combined organic layers were sequentially washed with H2O (40 mL) a 1N NaOH solution (40 mL), H2O (40 mL) and a saturated NaCl solution (40 mL), dried (Na2SO4) concentrated under reduced pressure The resulting powder was purified by crystalization (EtOAc)

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

Procedure: To a solution of 2-n-propylaniline (8.91 g, 66 mmol) and Et3N (14 mL, 106 mmol) in CH2Cl2 (60 mL) was added acetic anhydride (10.9 mL, 99 mmol) dropwise. The resulting mixture was allowed to stir at room temp. overnight, then was treated with a 1N HCl solution (40 mL). The acidic mixture was extracted with CH2Cl2 (2×30 mL). The combined organic layers were sequentially washed with H2O (40 mL), a 1N NaOH solution (40 mL), H2O (40 mL) and a saturated NaCl solution (40 mL), dried (Na2SO4), and concentrated under reduced pressure. The resulting powder was purified by crystalization (EtOAc) to give 2-n-propylacetanilide as white needles (7.85 g, 67%). TLC (30% EtOAc/hex) Rf0.37. The acidic mixture was extracted with CH2Cl2 (2×30 mL) The combined organic layers were sequentially washed with H2O (40 mL) a 1N NaOH solution (40 mL), H2O (40 mL) and a saturated NaCl solution (40 mL), dried (Na2SO4) concentrated under reduced pressure The resulting powder was purified by crystalization (EtOAc)

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

Procedure: To a solution of 2-n-propylaniline (8.91 g, 66 mmol) and Et3N (14 mL, 106 mmol) in CH2Cl2 (60 mL) was added acetic anhydride (10.9 mL, 99 mmol) dropwise. The resulting mixture was allowed to stir at room temp. overnight, then was treated with a 1N HCl solution (40 mL). The acidic mixture was extracted with CH2Cl2 (2×30 mL). The combined organic layers were sequentially washed with H2O (40 mL), a 1N NaOH solution (40 mL), H2O (40 mL) and a saturated NaCl solution (40 mL), dried (Na2SO4), and concentrated under reduced pressure. The resulting powder was purified by crystalization (EtOAc) to give 2-n-propylacetanilide as white needles (7.85 g, 67%). TLC (30% EtOAc/hex) Rf0.37. The acidic mixture was extracted with CH2Cl2 (2×30 mL) The combined organic layers were sequentially washed with H2O (40 mL) a 1N NaOH solution (40 mL), H2O (40 mL) and a saturated NaCl solution (40 mL), dried (Na2SO4) concentrated under reduced pressure The resulting powder was purified by crystalization (EtOAc)

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

Procedure: Acetyl chloride (5.6 ml) and triethylamine (12.5 ml) were added dropwise to a chloroform (50 ml) solution of 2-propylaniline (10.5 g) in this order under ice-cooling. The reaction solution was stirred at room temperature for 3 hours. The solution was concentrated under reduced pressure, and the thus-obtained solid was washed with water and collected by filtration. The resulting residue was recrystallized from ethanol-water to obtain 2-propylacetanilide (11.85 g; yield, 86%) as white crystals. cooling The solution was concentrated under reduced pressure the thus-obtained solid was washed with water collected by filtration The resulting residue was recrystallized from ethanol-water

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

Procedure: Acetic anhydride (7.5 ml) was added to a toluene (100 ml) solution of 2-propylaniline, and the mixture was stirred at room temperature for 2 hours. Crystals thus precipitated were collected by filtration and washed with hexane. The filtrate was concentrated under reduced pressure. After hexane was added thereto, tritulation was conducted. The deposited crystals were collected by filtration and washed with hexane. By the above crystallization steps, 2-propylacetanilide (13.0 g; yield, 96%) was obtained as white crystals. Crystals thus precipitated were collected by filtration washed with hexane The filtrate was concentrated under reduced pressure After hexane was added The deposited crystals were collected by filtration washed with hexane By the above crystallization steps

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

Procedure: To a solution of 2-n-propylaniline (8.91 g, 66 mmol) and Et3N (14 mL, 106 mmol) in CH2Cl2 (60 mL) was added acetic anhydride (10.9 mL, 99 mmol) dropwise. The resulting mixture was allowed to stir at room temp. overnight, then was treated with a 1N HCl solution (40 mL). The acidic mixture was extracted with CH2Cl2 (2×30 mL). The combined organic layers were sequentially washed with H2O (40 mL), a 1N NaOH solution (40 mL), H2O (40 mL) and a saturated NaCl solution (40 mL), dried (Na2SO4), and concentrated under reduced pressure. The resulting powder was purified by crystalization (EtOAc) to give 2-n-propylacetanilide as white needles (7.85 g, 67%). TLC (30% EtOAc/hex) Rf0.37. The acidic mixture was extracted with CH2Cl2 (2×30 mL) The combined organic layers were sequentially washed with H2O (40 mL) a 1N NaOH solution (40 mL), H2O (40 mL) and a saturated NaCl solution (40 mL), dried (Na2SO4) concentrated under reduced pressure The resulting powder was purified by crystalization (EtOAc)