2-氯苯-1,3-二胺

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: 11.0 g. of dimethylacetylene dicarboxylate is added dropwise to a solution of 5.25 g. of 2-chloro-1,3-diaminobenzene in 100 ml. of methanol at room temperature. The mixture is stirred for 2 hours at room temperature and the resulting yellow solid is collected by filtration. The solid is washed with 20 to 50 ml. of methanol, dried under vacuum at 60° C., and recrystallized from acetone. The tetramethyl[2-chloro-m-phenylene-diamino]dimaleate melts at 202.5°-204.5°C. at room temperature the resulting yellow solid is collected by filtration The solid is washed with 20 to 50 ml of methanol, dried under vacuum at 60° C. recrystallized from acetone

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: 11.0 g. of dimethylacetylene dicarboxylate is added dropwise to a solution of 5.25 g. of 2-chloro-1,3-diaminobenzene in 100 ml. of methanol at room temperature. The mixture is stirred for 2 hours at room temperature and the resulting yellow solid is collected by filtration. The solid is washed with 20 to 50 ml. of methanol, dried under vacuum at 60° C., and recrystallized from acetone. The tetramethyl[2-chloro-m-phenylene-diamino]dimaleate melts at 202.5°-204.5°C. at room temperature the resulting yellow solid is collected by filtration The solid is washed with 20 to 50 ml of methanol, dried under vacuum at 60° C. recrystallized from acetone

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: A solution of 1 ml. of concentrated hydrochloric acid in 5 ml. of 5% ethanol is slowly added to a refluxing mixture of 10.1 g. of 1-chloro-2,6-dinitrobenzene, electrolytically reduced iron and 20 ml. of 50% ethanol. The mixture is heated at reflux for 2 hours. The mixture is allowed to cool slightly and the pH is adjusted to 8 with sodium hydroxide solution. The iron products are removed by filtration. The solvent is removed from the filtrate to leave a solid which is dissolved in water and extracted with methylene chloride. Removal of the solvents leaves an oily solid which upon recrystallization of from Skellysolve B gives off-white crystals of 2-chloro-1,3-diaminobenzene having a melting point of 82°-83.5° C. The mixture is heated at reflux for 2 hours to cool slightly The iron products are removed by filtration The solvent is removed from the filtrate to leave a solid which extracted with methylene chloride Removal of the solvents leaves an oily solid which upon recrystallization of from Skellysolve B

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: To a mixture of 2-chlorobenzene-1,3-diamine (24 mmol) (CAS 6400-14-2) and NaI (150 mg) in 80% H2SO4 (20 g) was added Glycerol (45 g). The mixture was stirred at 150° C. to 170° C. for 5 h. The mixture was cooled to room temperature. Aqueous 5N NaOH was used to adjust the pH to alkaline, which was then extracted with EtOAc washed with brine, dried over MgSO4 and concentrated under reduced vacuum. Flash column chromatography (EtOAc:Hexane) yielded 7-amino-8-chloroquinoline (800 mg), as a pale yellow solid. 1H NMR (300 MHz, CD3OD) δ: 8.69 (dd, J=4.4, 1.8 Hz, 1H), 8.13 (dd, J=7.9, 1.8 Hz, 1H), 7.61 (d, J=9.1 Hz, 1H), 7.14-7.29 (m, 2H) which was then extracted with EtOAc washed with brine dried over MgSO4 concentrated under reduced vacuum

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: A solution of 1 ml. of concentrated hydrochloric acid in 5 ml. of 5% ethanol is slowly added to a refluxing mixture of 10.1 g. of 1-chloro-2,6-dinitrobenzene, electrolytically reduced iron and 20 ml. of 50% ethanol. The mixture is heated at reflux for two hours. The mixture is allowed to cool slightly and the pH is adjusted to 8 with sodium hydroxide solution. The iron products are removed by filtration. The solvent is removed from the filtrate to leave a solid which is dissolved in water and extracted with methylene chloride. Removal of the solvents leaves an oily solid which upon recrystallization of from Skellysolve B gives off-white crystals of 2-chloro-1,3-diaminobenzene having a melting point of 82°-83.5° C. The mixture is heated at reflux for two hours to cool slightly The iron products are removed by filtration The solvent is removed from the filtrate to leave a solid which extracted with methylene chloride Removal of the solvents leaves an oily solid which upon recrystallization of from Skellysolve B

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: 11.0 g. of dimethylacetylene dicarboxylate is added dropwise to a solution of 5.25 g. of 2-chloro-1,3-diaminobenzene in 100 ml. of methanol at room temperature. The mixture is stirred for 2 hours at room temperature and the resulting yellow solid is collected by filtration. The solid is washed with 20 to 50 ml. of methanol, dried under vacuum at 60° C., and recrystallized from acetone. The tetramethyl[2-chloro-m-phenylene-diamino]dimaleate melts at 202.5°-204.5°C. at room temperature the resulting yellow solid is collected by filtration The solid is washed with 20 to 50 ml of methanol, dried under vacuum at 60° C. recrystallized from acetone

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: A solution of 1 ml. of concentrated hydrochloric acid in 5 ml. of 5% ethanol is slowly added to a refluxing mixture of 10.1 g. of 1-chloro-2,6-dinitrobenzene, electrolytically reduced iron and 20 ml. of 50% ethanol. The mixture is heated at reflux for 2 hours. The mixture is allowed to cool slightly and the pH is adjusted to 8 with sodium hydroxide solution. The iron products are removed by filtration. The solvent is removed from the filtrate to leave a solid which is dissolved in water and extracted with methylene chloride. Removal of the solvents leaves an oily solid which upon recrystallization of from Skellysolve B gives off-white crystals of 2-chloro-1,3-diaminobenzene having a melting point of 82°-83.5° C. The mixture is heated at reflux for 2 hours to cool slightly The iron products are removed by filtration The solvent is removed from the filtrate to leave a solid which extracted with methylene chloride Removal of the solvents leaves an oily solid which upon recrystallization of from Skellysolve B

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: To a mixture of 2-chlorobenzene-1,3-diamine (24 mmol) (CAS 6400-14-2) and NaI (150 mg) in 80% H2SO4 (20 g) was added Glycerol (45 g). The mixture was stirred at 150° C. to 170° C. for 5 h. The mixture was cooled to room temperature. Aqueous 5N NaOH was used to adjust the pH to alkaline, which was then extracted with EtOAc washed with brine, dried over MgSO4 and concentrated under reduced vacuum. Flash column chromatography (EtOAc:Hexane) yielded 7-amino-8-chloroquinoline (800 mg), as a pale yellow solid. 1H NMR (300 MHz, CD3OD) δ: 8.69 (dd, J=4.4, 1.8 Hz, 1H), 8.13 (dd, J=7.9, 1.8 Hz, 1H), 7.61 (d, J=9.1 Hz, 1H), 7.14-7.29 (m, 2H) which was then extracted with EtOAc washed with brine dried over MgSO4 concentrated under reduced vacuum