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With N-chloro-succinimide; acetic acid; at 0.55 - 50℃;Inert atmosphere; |
4-Chloro-2-methyl-6-nitroaniline (B) To a 2-necked round-bottom flask equipped with an addition funnel, a thermometer and a magnetic stir bar under an atmosphere of argon, was added 2-methyl-6-nitroaniline (12.97 g; 85.23 mmol) and glacial acetic acid (35 mL). The suspension was placed in a pre-heated oil bath at 50 C. to produce a red solution. To the addition funnel was added a suspension of 11.95 g N-chlorosuccinimide (NCS) in about 45 mL of acetic acid. The NCS suspension was added dropwise over about 15 minutes while maintaining the temperature at about 55 C. After the addition was complete, the addition funnel was rinsed with acetic acid (ca. 5 mL) and added to the reaction mixture. A brown homogeneous solution resulted during the course of the reaction. The progress of the reaction was followed by TLC (eluent: methylene chloride). Upon completion of the reaction, the reaction mixture was cooled to room temperature and poured into 100 mL of water and then cooled in an ice bath. The solids were filtered on paper under vacuum, and rinsed with 130 mL of water. The solids were dried in the filter funnel under vacuum to yield 13.3 g of the title compound as an orange-red solid. 1H NMR (400 MHz, DMSO-d6) delta 7.82 (d, J=2.2 Hz, 1H), 7.38 (br. s, 1H), 7.23 (br. s., 2H), 2.17 (s, 3H). MS (ESI+) m/z=187 (M+1). This material was used in the subsequent reactions without further purification. |
| 13.3 g |
With N-chloro-succinimide; acetic acid; at 50 - 55℃;Inert atmosphere; |
To a 2-necked round-bottom flask equipped with an addition funnel,a thermometer and a magnetic stir bar under an Argon atmosphere wasadded 12.97 g (85.23 mmol) of 2-methyl-6-nitroaniline and 35 mLglacial acetic acid. The suspension was placed in a pre-heated oil bathat 50 C to produce a red solution. To the addition funnel was added asuspension of 11.95 g N-chlorosuccinimide (NCS) in ca. 45 mL of aceticacid. The NCS suspension was added dropwise over ca 15 min whilemaintaining the temperature around 55 C. After the addition wascomplete, the addition funnel was rinsed with acetic acid (ca. 5 mL) andadded. A brown homogeneous solution resulted during the course of thereaction. The progress of the reaction was followed by TLC using methylenechloride as the elutant. Upon completion of the reaction, thereaction mixture was cooled to room temperature, poured into 100 mLof water and cooled in an ice bath. The solids were filtered on paperunder vacuum, and rinsed with a total of 130 mL of water. The solidswere dried in air in the filter funnel under vacuum to yield 13.3 g of 4-chloro-2-methyl-6-nitroaniline as an orange-red solid. 1H NMR(400 MHz, DMSO-d6) delta 7.82 (d, J=2.2 Hz, 1H), 7.38 (br. s, 1H), 7.23(br. s., 2H), 2.17 (s, 3H). MS (ESI+) m/z=187 (M+1). This materialwas used in the subsequent reaction without further purification. |
|
With N-chloro-succinimide; acetic acid; at 50 - 55℃;Inert atmosphere; |
To a 2-necked round-bottom flask equipped with an addition funnel, a thermometer and a magnetic stir bar under an Argon atmosphere was added 12.97 g (85.23 mmol) of 2- methyl-6-nitroaniline and 35 ml glacial acetic acid. The suspension was placed in a pre- heated oil bath at 50 C to produce a red solution. To the addition funnel was added a suspension of 11.95 g N-chlorosuccinimide (NCS) in ca.45 mL of acetic acid. The NCS suspension was added dropwise over ca.15 minutes while maintaining the temperature around 55 C. After the addition was complete, the addition funnel was rinsed with acetic acid (ca.5 mL) and added. A brown homogeneous solution resulted during the course of the reaction. The progress of the reaction was followed by TLC using methylene chloride as the elutant. Upon completion of the reaction, the reaction mixture was cooled to room temperature, poured into 100 mL of water and cooled in an ice bath. The solids were filtered on paper under vacuum, and rinsed with a total of 130 mL of water. The solids were dried in air in the filter funnel under vacuum to yield 13.3 g of 4-chloro-2-methyl-6-nitroaniline as an orange-red solid. 1H NMR (400 MHz, DMSO-d6) 7.82 (d, J = 2.2 Hz, 1H), 7.38 (br. s, 1H), 7.23 (br. s., 2H), 2.17 (s, 3H). MS (ESI+) m/z = 187 (M+1). This material was used in the subsequent reaction without further purification. |
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