5-溴-3-乙苯-1,2-二胺

反应条件: temp:62.51; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: A mixture of 1,2-diamino-4-bromo-6-ethylbenzene (40 mg, 0.14 mmol) and oxalic acid dihydrate (25 mg, 0.20 mmol, used as received) in 4 N HCl (1.5 mL) was refluxed at 120-5° C. for 3 h, then cooled to room temperature. The mixture was centrifuged and the liquid layer was removed. The yellow solid was washed with cold water (2×1 mL), collected by filtration, and dried at 60° C. under reduced pressure for 2 h, affording 40 mg of crude product (80%) as a yellow powder. The crude product was dissolved in 1N NaOH (2 mL) and filtered. The filtrate was acidified to pH=5, affording 12 mg of pure title compound; mp: >350° C. (dec. from 300° C.), IR (KBr, cm−1):3410, 3164, 2919, 1740, 1705, 1600. 1H NMR (DMSO-d6): 1.099 (t, 3 H; J=6 Hz), 2.741 (q, 2 H, J=7.2 Hz), 7.117, (d, 1 H, J=1.8 Hz), 7.138 (d, 1 H, J=1.8 Hz); 11.343 (s, 1H); 11.958 (s, 1H). HRMS: calcd for C10H9BrN2O2 (M+) m/z: 267.9846; found 267.9853. cooled to room temperature the liquid layer was removed The yellow solid was washed with cold water (2×1 mL) collected by filtration dried at 60° C. under reduced pressure for 2 h affording 40 mg of crude product (80%) as a yellow powder filtered

反应条件: temp:62.51; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: A mixture of 1,2-diamino-4-bromo-6-ethylbenzene (40 mg, 0.14 mmol) and oxalic acid dihydrate (25 mg, 0.20 mmol, used as received) in 4 N HCl (1.5 mL) was refluxed at 120-5° C. for 3 h, then cooled to room temperature. The mixture was centrifuged and the liquid layer was removed. The yellow solid was washed with cold water (2×1 mL), collected by filtration, and dried at 60° C. under reduced pressure for 2 h, affording 40 mg of crude product (80%) as a yellow powder. The crude product was dissolved in 1N NaOH (2 mL) and filtered. The filtrate was acidified to pH=5, affording 12 mg of pure title compound; mp: >350° C. (dec. from 300° C.), IR (KBr, cm−1):3410, 3164, 2919, 1740, 1705, 1600. 1H NMR (DMSO-d6): 1.099 (t, 3 H; J=6 Hz), 2.741 (q, 2 H, J=7.2 Hz), 7.117, (d, 1 H, J=1.8 Hz), 7.138 (d, 1 H, J=1.8 Hz); 11.343 (s, 1H); 11.958 (s, 1H). HRMS: calcd for C10H9BrN2O2 (M+) m/z: 267.9846; found 267.9853. cooled to room temperature the liquid layer was removed The yellow solid was washed with cold water (2×1 mL) collected by filtration dried at 60° C. under reduced pressure for 2 h affording 40 mg of crude product (80%) as a yellow powder filtered

反应条件: temp:62.51; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: A mixture of 1,2-diamino-4-bromo-6-ethylbenzene (40 mg, 0.14 mmol) and oxalic acid dihydrate (25 mg, 0.20 mmol, used as received) in 4 N HCl (1.5 mL) was refluxed at 120-5° C. for 3 h, then cooled to room temperature. The mixture was centrifuged and the liquid layer was removed. The yellow solid was washed with cold water (2×1 mL), collected by filtration, and dried at 60° C. under reduced pressure for 2 h, affording 40 mg of crude product (80%) as a yellow powder. The crude product was dissolved in 1N NaOH (2 mL) and filtered. The filtrate was acidified to pH=5, affording 12 mg of pure title compound; mp:>350° C. (dec. from 300° C.); IR (KBr, cm-1):3410, 3164, 2919, 1740, 1705, 1600. 1H NMR (DMSO-d6): δ 1.099 (t, 3 H, J=6 Hz), 2.741 (q, 2 H, J=7.2 Hz), 7.117 (d, 1 H, J=1.8 Hz), 7.138 (d, 1 H, J=1.8 Hz); 11.343 (s, 1H); 11.958 (s, 1H). HRMS: calcd for C10H9BrN2O2 (M+) m/z: 267.9846; found 267.9853. cooled to room temperature the liquid layer was removed The yellow solid was washed with cold water (2×1 mL) collected by filtration dried at 60° C. under reduced pressure for 2 h affording 40 mg of crude product (80%) as a yellow powder filtered

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

实验步骤: A mixture of 1,2-diamino-4-bromo-6-ethylbenzene (40 mg, 0.14 mmol) and oxalic acid dihydrate (25 mg, 0.20 mmol, used as received) in 4N HCl (1.5 mL) was refluxed at 120°-5° C. for 3 h, then cooled to room temperature. The mixture was centrifuged and the liquid layer was removed. The yellow solid was washed with cold water (2×1 mL), collected by filtration, and dried at 60° C. under reduced pressure for 2 h, affording 40 mg of crude product (80%) as a yellow powder. The crude product was dissolved in 1N NaOH (2 mL) and filtered. The filtrate was acidified to pH=5, affording 12 mg of pure title compound; mp: >350° C. (dec. from 300° C.); IR (KBr, cm-1): 3410, 3164, 2919, 1740, 1705, 1600. 1H NMR (DMSO-d6): δ1.099 (t, 3H, J=6 Hz), 2.741 (q, 2H, J=7.2 Hz), 7.117 (d, 1H, J=1.8 Hz), 7,138 (d, 1H, J=1.8 Hz); 11.343 (s, 1H); 11.958 (s, 1H). HRMS: calcd for C10H9BrN2O2 (M+) m/z: 267.9846; found 267.9853. was refluxed at 120°-5° C. for 3 h the liquid layer was removed The yellow solid was washed with cold water (2×1 mL) collected by filtration dried at 60° C. under reduced pressure for 2 h affording 40 mg of crude product (80%) as a yellow powder filtered

反应条件: temp:62.51; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: A mixture of 1,2-diamino-4-bromo-6-ethylbenzene (40 mg, 0.14 mmol) and oxalic acid dihydrate (25 mg, 0.20 mmol, used as received) in 4N HCl (1.5 mL) was refluxed at 120-5° C. for 3 h, then cooled to room temperature. The mixture was centrifuged and the liquid layer was removed. The yellow solid was washed with cold water (2×1 mL), collected by filtration, and dried at 60° C. under reduced pressure for 2 h, affording 40 mg of crude product (80%) as a yellow powder. The crude product was dissolved in 1N NaOH (2 mL) and filtered. The filtrate was acidified to pH=5, affording 12 mg of pure title compound; mp: >350° C. (dec. from 300° C.); IR (KBr, cm-1):3410, 3164, 2919, 1740, 1705, 1600. 1H NMR (DMSO-d6): δ 1.099 (t, 3H; J=6 Hz), 2.741 (q, 2H, J=7.2 Hz), 7.117 (d, 1H, J=1.8 Hz), 7.138 (d, 1H, J=1.8 Hz); 11.343 (s, 1H); 11.958 (s, 1H). HRMS: calcd for C10H9BrN2O2 (M+) m/z: 267.9846; found 267.9853. cooled to room temperature the liquid layer was removed The yellow solid was washed with cold water (2×1 mL) collected by filtration dried at 60° C. under reduced pressure for 2 h affording 40 mg of crude product (80%) as a yellow powder filtered

反应条件: temp:62.51; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: A mixture of 1,2-diamino-4-bromo-6-ethylbenzene (40 mg, 0.14 mmol) and oxalic acid dihydrate (25 mg, 0.20 mmol, used as received) in 4 N HCl (1.5 mL) was refluxed at 120-5° C. for 3 h, then cooled to room temperature. The mixture was centrifuged and the liquid layer was removed. The yellow solid was washed with cold water (2×1 mL), collected by filtration, and dried at 60° C. under reduced pressure for 2 h, affording 40 mg of crude product (80%) as a yellow powder. The crude product was dissolved in 1N NaOH (2 mL) and filtered. The filtrate was acidified to pH=5, affording 12 mg of pure title compound; mp: >350° C. (dec. from 300° C.), IR (KBr, cm−1):3410, 3164, 2919, 1740, 1705, 1600. 1H NMR (DMSO-d6): 1.099 (t, 3 H; J=6 Hz), 2.741 (q, 2 H, J=7.2 Hz), 7.117, (d, 1 H, J=1.8 Hz), 7.138 (d, 1 H, J=1.8 Hz); 11.343 (s, 1H); 11.958 (s, 1H). HRMS: calcd for C10H9BrN2O2 (M+) m/z: 267.9846; found 267.9853. cooled to room temperature the liquid layer was removed The yellow solid was washed with cold water (2×1 mL) collected by filtration dried at 60° C. under reduced pressure for 2 h affording 40 mg of crude product (80%) as a yellow powder filtered