N-(3-amino-4-methylphenyl)acetamide

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

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: N-(5-Acetylamino-2-methyl-phenyl)-2,2,2-trifluoro-acetamide (2.93 g, 11.24 mmol) was taken up in methanol (50 mL) and sodium carbonate (5.96 g, 56.20 mmol) was added. The reaction was stirred at room temp for 12 h. The reaction mixture was into water and the aqueous layer was extracted three times with ethyl acetate. The combined organic layers were washed with brine and dried over anhydrous magnesium sulfate. The solution was filtered and the solvent removed under reduced pressure. The product was utilized without further purification. Yield 1.60 g. 1H NMR (CDCl3, 300 MHz): δ2.16 (s, 3H). 2.31 (s, 3H), 7.18 (d, J=9 Hz, 1H), 7.32 (d, J 9 Hz, 1H), 7.64 (s, 1H), 7.64 (s, 1H). the aqueous layer was extracted three times with ethyl acetate The combined organic layers were washed with brine dried over anhydrous magnesium sulfate The solution was filtered the solvent removed under reduced pressure The product was utilized without further purification

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

Procedure: N-(5-Acetylamino-2-methyl-phenyl)-2,2,2-trifluoro-acetamide (2.93 g, 11.24 mmol) was taken up in methanol (50 mL) and sodium carbonate (5.96 g, 56.20 mmol) was added. The reaction was stirred at room temp for 12 h. The reaction mixture was into water and the aqueous layer was extracted three times with ethyl acetate. The combined organic layers were washed with brine and dried over anhydrous magnesium sulfate. The solution was filtered and the solvent removed under reduced pressure. The product was utilized without further purification. Yield 1.60 g. 1H NMR (CDCl3, 300 MHz): δ2.16 (s, 3H). 2.31 (s, 3H), 7.18 (d, J=9 Hz, 1H), 7.32 (d, J 9 Hz, 1H), 7.64 (s, 1H), 7.64 (s, 1H). the aqueous layer was extracted three times with ethyl acetate The combined organic layers were washed with brine dried over anhydrous magnesium sulfate The solution was filtered the solvent removed under reduced pressure The product was utilized without further purification

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

Procedure: 4-acetamino-2-aminotoluene or -2-aminoanisole;

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

Procedure: 4-acetamino-2-aminotoluene or 2-aminoanisole;

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

Procedure: 4-acetamino-2-aminotoluene or 2-aminoanisole;

Conditions: temp:80.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 38.2 Parts 1-amino-4-bromoanthraquinone-2-sulphonic acid are dissolved in 200 parts water/100 parts i-propanol and the pH adjusted to 8.5-9.0 with sodium carbonate. After addition of 18 parts 4-acetylamino-2-aminotoluene the mixture is warmed to 80° C. and treated with 1 part cuprous chloride and 12 parts sodium carbonate. After 4 hours the reaction is over. Finally 25 parts 30% hydrochloric acid are added to the reaction mixture, which is then heated to reflux. After 18 hours the suspension is cooled to room temperature, filtered and washed with 1% hydrochloric acid, to give 1-amino-4-(5'-amino-2'-methylphenylamino)-anthraquinone-2-sulphonic acid. is then heated to reflux After 18 hours the suspension is cooled to room temperature filtered washed with 1% hydrochloric acid

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

Procedure: 2-Methyl-5-acetamido aniline (49.2 g, 0.3 m), triethyl amine (32.7 g, 0.3 m) and p-dioxane (350 ml) are stirred together at room temperature. 2-Chloroethane sulfonylfluoride (43.0 g, 0.3 m) is added dropwise allowing temperature to rise to 45° C. The reaction mixture is then heated at reflux for 3 hrs. When thin-layer chromatography shows reaction to be complete, the reaction is allowed to cool and then drowned into water (2000 ml). The product is collected by filtration, washed with water and melts at 154°-155° C. to rise to 45° C The reaction mixture is then heated at reflux for 3 hrs reaction to cool The product is collected by filtration washed with water and melts at 154°-155° C.

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

Procedure: 2-Methyl-5-acetamido aniline (49.2 g, 0.3 m), triethyl amine (32.7 g, 0.3 m) and p-dioxane (350 ml) are stirred together at room temperature. 2-Chloroethane sulfonylfluoride (43.0 g, 0.3 m) is added dropwise allowing temperature to rise to 45° C. The reaction mixture is then heated at reflux for 3 hrs. When thin-layer chromatography shows reaction to be complete, the reaction is allowed to cool and then drowned into water (2000 ml). The product is collected by filtration, washed with water and melts at 154°-155° C. to rise to 45° C The reaction mixture is then heated at reflux for 3 hrs reaction to cool The product is collected by filtration washed with water and melts at 154°-155° C.

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

Procedure: To a solution of N-(3-amino-4-methyl-phenyl)acetamide (5 g, 25 mmol) in DMF (5 mL) was added 2-chloropyrimidine (3.8 g, 33 mmol) and KI (0.5 g). The reaction was stirred at 100° C. overnight, cooled to 10° C. (100 mL). The resulting mixture was extracted with CH2Cl2 (2×100 mL). The combined organic layers were dried (Na2SO4) and concentrated under vacuum. The residue was dissolved in conc. HCl (10 mL), stirred at 80° C. for 2 h and concentrated under vacuum to yield 6-methyl-N′-(pyrimidin-2-yl)benzene-1,3-diamine hydrochloride (3.75 g, 75% yield). 1H NMR (400 MHz, CDCl3): 8.36 (dd, J=15.2, 4.8 Hz, 2H), 7.46 (d, J=2.4 Hz, 1H), 6.97 (d, J=8.0 Hz, 1H), 7.26 (s, 1H), 6.67 (t, J=4.8 Hz, 1H), 6.39 (dd, J=8.0, 2.4, Hz, 1H), 2.20 (s, 3H); MS (ESI) m/e: 201 (M+H+). cooled to 10° C. (100 mL) The resulting mixture was extracted with CH2Cl2 (2×100 mL) The combined organic layers were dried (Na2SO4) concentrated under vacuum The residue was dissolved in conc. HCl (10 mL) stirred at 80° C. for 2 h concentrated under vacuum