2-methylsulfanylaniline

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

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

Procedure: 4-Methylthiooxindole and 6-methylthiooxindole are prepared according to the procedure of U.S. Pat. No. 4,006,161. 7-Methylthio and 7-n-butylthiooxindoles are prepared by using the same procedure starting with 2-methylthioaniline and 2-n-butylthioaniline, respectively. 5-n-Propylthiooxindole is prepared by the same synthetic route starting with 4-n-propylthioaniline.

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

Procedure: 2-(Methylmercapto)aniline (23.6 g, 169.5 mmol) was suspended in conc. HCl (200 mL) and trifluoroacetic acid (130 mL), and cooled to 0° C. in an ice bath. Sodium nitrite (14.0 g, 203.4 mmol) was dissolved in water (45 mL) and added dropwise to the suspension over 45 minutes. After the addition, the reaction was stirred at 0° C. for 1 h. In a separate flask, tin (II) chloride (76 g, 338.4 mmol) was dissolved in conc. HCl (100 mL) and added slowly over 15 minutes to the reaction mixture. The resultant suspension was warmed to room temperature and stirred for 48 hours. The reaction was filtered, washed with isopropyl alcohol (15 mL), and dried to give 1-[2-(methylsulfanyl)phenyl]hydrazine hydrochloride (30 g, 93%). 1H NMR (CD3OD, 300 MHz) δ 7.44 (d, 1H, J=7.7 Hz), 7.32-7.26 (m, 1H), 7.08-7.00 (m, 2H), 2.39 (s, 3H) ppm. added dropwise to the suspension over 45 minutes After the addition added slowly over 15 minutes to the reaction mixture stirred for 48 hours The reaction was filtered washed with isopropyl alcohol (15 mL) dried

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

Procedure: The method of Example 312 was used as well as 0.3 g of 4-chloro-6-methoxy-7-(3-morpholin-4-yl-propoxy)-quinoline-3-carbonitrile, 0.14 ml of 2-(methyl mercapto) aniline, 0.1 g of pyridine hydrochloride and 4.0 ml of 2-ethoxy ethanol. This afforded an oil which was purified by silica gel flash chromatography [methylene chloride/methanol (96:4) ] to give 0.16 g of the title compound as an off white solid, mp 179-180 C; mass spectrum (ES, m/e):M+H465. This afforded an oil which was purified by silica gel flash chromatography [methylene chloride/methanol (96:4) ]

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

Procedure: A mixture of 0.249 g of 4-chloro-6,7-dimethoxy-3-quinolinecarbonitrile, 0.139 g of 2-(methylmercapto)aniline, 20 mg of pyridine hydrochloride, and 10 ml of ethoxyethanol was stirred under nitrogen, at reflux temperature for 30 minutes. The mixture was cooled and added to 40 ml of water. To this mixture was added sodium carbonate and concentrated hydrogen chloride to adjust pH to 7. The product was collected, washed with water, and dried to give 0.184 g of 6,7-dimethoxy-4-(2-methylsulfanyl-phenylamino)-quinoline-3-carbonitrile as a solid, mp 245-247° C.; mass spectrum (EI, m/e): M 351.1051. at reflux temperature for 30 minutes The mixture was cooled The product was collected washed with water dried

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

Procedure: 4-Methylthiooxindole and 6-methylthiooxindole are prepared according to the procedure of U.S. Pat. No. 4,006,161. 7-Methylthio and 7-n-butylthiooxindoles are prepared by using the same procedure starting with 2-methylthioaniline and 2-n-butylthioaniline, respectively. 5-n-Propylthiooxindole is prepared by the same synthetic route starting with 4-n-propylthioaniline.

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

Procedure: 4-Methylthiooxindole and 6-methylthiooxindole are prepared according to the procedure of U.S. Pat. No. 4,006,161. 7-Methylthio and 7-n-butylthiooxindoles are prepared by using the same procedure starting with 2-methylthioaniline and 2-n-butylthioaniline, respectively. 5-n-Propylthiooxindole is prepared by the same synthetic route starting with 4-n-propylthioaniline.

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

Procedure: 2-(amino)thiophenol and 2-(methylthio)aniline were purchased from Aldrich Chemical Company.

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

Procedure: 4-Methylthiooxindole and 6-methylthiooxindole are prepared according to the procedure of U.S. Pat. No. 4,006,161. 7-Methylthio and 7-n-butylthiooxindoles are prepared by using the same procedure starting with 2-methylthioaniline and 2-n-butylthioaniline, respectively. 5-n-Propylthiooxindole is prepared by the same synthetic route starting with 4-n-propylthioaniline.

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

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

Procedure: 2-(amino)thiophenol and 2-(methylthio)aniline were purchased from Aldrich Chemical Company.

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

Procedure: 4-Methylthiooxindole and 6-methylthiooxindole are prepared according to the procedure of U.S. Pat. No. 4,006,161. 7-Methylthio and 7-n-butylthiooxindoles are prepared by using the same procedure starting with 2-methylthioaniline and 2-n-butylthioaniline, respectively. 5-n-Propylthiooxindole is prepared by the same synthetic route starting with 4-n-propylthioaniline.