2-(3-oxo-2,4-dihydro-1H-quinoxalin-2-yl)acetamide

Conditions: temp:95.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of 1,2-phenylenediamine (21.5 g, 0.2 mol) in water (450 mL) was added dropwise a solution of maleimide, (20.0 g, 0.2 mol) in methanol (180 mL) over 60 min. The mixture was then stirred at 95° C. for 2 hours followed at rt overnight. The precipitate was collected via filtration and was washed with small amount of water for a few times to yield the title compound as a pale gray solid (pure product): 1H NMR (DMSO-d6) δ=10.2 (bs, 1H), 7.37 (bs, 1H) 6.88 (bs, 1H), 6.74–6.68 (m, 3H), 6.31–6.57 (m, 1H), 5.78 (bs, 1H), 4.08–4.04 (m, 1H), 2.63 (dd, 1H, J=3.6, 15.5 Hz), 2.32 (dd, 1H, J=3.3, 15.5 Hz); HPLC (CH3CN—H2O-0.1% TFA): Rf=9.49 min. followed at rt overnight The precipitate was collected via filtration was washed with small amount of water for a few times

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

Procedure: 2-(3-Oxo-1,2,3,4-tetrahydroquinoxalin-2-yl)-acetamide (22 g, 0.11 mol) was dissolved in 10% NaOH (600 mL) and was heated under reflux for 3 hours. The mixture was cooled down via an ice-bath and was acidified with pre-cooled 10% HCl to pH -6. The solvent was concentrated and the resulting precipitate was isolated via filtration to give a gray solid as the title product: 1H NMR (DMSO-d6) δ=12.35 (bs, 1H), 10.25 (bs, 1H), 6.74–6.68 (m, 3H), 6.61–6.58 (m, 1H), 5.91 (bs, 1H), 4.08–4.04 (m, 1H), 2.69 (dd, 1H, J=5.1, 16.2 Hz), 2.51 (dd, 1H, J=6.9, 16.2 Hz) was heated under reflux for 3 hours The mixture was cooled down via an ice-bath The solvent was concentrated the resulting precipitate was isolated via filtration

Conditions: temp:95.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of 1,2-phenylenediamine (21.5 g, 0.2 mol) in water (450 mL) was added dropwise a solution of maleimide, (20.0 g, 0.2 mol) in methanol (180 mL) over 60 min. The mixture was then stirred at 95° C. for 2 hours followed at rt overnight. The precipitate was collected via filtration and was washed with small amount of water for a few times to yield the title compound as a pale gray solid (pure product): 1H NMR (DMSO-d6) δ=10.2 (bs, 1H), 7.37 (bs, 1H) 6.88 (bs, 1H), 6.74–6.68 (m, 3H), 6.31–6.57 (m, 1H), 5.78 (bs, 1H), 4.08–4.04 (m, 1H), 2.63 (dd, 1H, J=3.6, 15.5 Hz), 2.32 (dd, 1H, J=3.3, 15.5 Hz); HPLC (CH3CN—H2O-0.1% TFA): Rf=9.49 min. followed at rt overnight The precipitate was collected via filtration was washed with small amount of water for a few times

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

Procedure: 2-(3-Oxo-1,2,3,4-tetrahydroquinoxalin-2-yl)-acetamide (22 g, 0.11 mol) was dissolved in 10% NaOH (600 mL) and was heated under reflux for 3 hours. The mixture was cooled down via an ice-bath and was acidified with pre-cooled 10% HCl to pH -6. The solvent was concentrated and the resulting precipitate was isolated via filtration to give a gray solid as the title product: 1H NMR (DMSO-d6) δ=12.35 (bs, 1H), 10.25 (bs, 1H), 6.74–6.68 (m, 3H), 6.61–6.58 (m, 1H), 5.91 (bs, 1H), 4.08–4.04 (m, 1H), 2.69 (dd, 1H, J=5.1, 16.2 Hz), 2.51 (dd, 1H, J=6.9, 16.2 Hz) was heated under reflux for 3 hours The mixture was cooled down via an ice-bath The solvent was concentrated the resulting precipitate was isolated via filtration

Conditions: temp:95.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of 1,2-phenylenediamine (21.5 g, 0.2 mol) in water (450 mL) was added dropwise a solution of maleimide, (20.0 g, 0.2 mol) in methanol (180 mL) over 60 min. The mixture was then stirred at 95° C. for 2 hours followed at rt overnight. The precipitate was collected via filtration and was washed with small amount of water for a few times to yield the title compound as a pale gray solid (pure product): 1H NMR (DMSO-d6) δ=10.2 (bs, 1H), 7.37 (bs, 1H) 6.88 (bs, 1H), 6.74-6.68 (m, 3H), 6.31-6.57 (m, 1H), 5.78 (bs, 1H), 4.08-4.04 (m, 1H), 2.63 (dd, 1H, J=3.6, 15.5 Hz), 2.32 (dd, 1H, J=3.3, 15.5 Hz); HPLC (CH3CN—H2O-0.1% TFA): Rf=9.49 min. followed at rt overnight The precipitate was collected via filtration was washed with small amount of water for a few times

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

Procedure: 2-(3-Oxo-1,2,3,4-tetrahydroquinoxalin-2-yl)-acetamide (22 g, 0.11 mol) was dissolved in 10% NaOH (600 mL) and was heated under reflux for 3 hours. The mixture was cooled down via an ice-bath and was acidified with pre-cooled 10% HCl to pH˜6. The solvent was concentrated and the resulting precipitate was isolated via filtration to give a gray solid as the title product: 1H NMR (DMSO-d6) δ=12.35 (bs, 1H), 10.25 (bs, 1H), 6.74-6.68 (m, 3H), 6.61-6.58 (m, 1H), 5.91 (bs, 1H), 4.08-4.04 (m, 1H), 2.69 (dd, 1H, J=5.1, 16.2 Hz), 2.51 (dd, 1H, J=6.9, 16.2 Hz) was heated under reflux for 3 hours The mixture was cooled down via an ice-bath The solvent was concentrated the resulting precipitate was isolated via filtration

Conditions: temp:95.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of 1,2-phenylenediamine (21.5 g, 0.2 mol) in water (450 mL) was added dropwise a solution of maleimide, (20.0 g, 0.2 mol) in methanol (180 mL) over 60 min. The mixture was then stirred at 95° C. for 2 hours followed at rt overnight. The precipitate was collected via filtration and was washed with small amount of water for a few times to yield the title compound as a pale gray solid (pure product): 1H NMR (DMSO-d6) δ=10.2 (bs, 1H), 7.37 (bs, 1H) 6.88 (bs, 1H), 6.74–6.68 (m, 3H), 6.31–6.57 (m, 1H), 5.78 (bs, 1H), 4.08–4.04 (m, 1H), 2.63 (dd, 1H, J=3.6, 15.5 Hz), 2.32 (dd, 1H, J=3.3, 15.5 Hz); HPLC (CH3CN—H2O-0.1% TFA): Rf=9.49 min. followed at rt overnight The precipitate was collected via filtration was washed with small amount of water for a few times

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

Procedure: 2-(3-Oxo-1,2,3,4-tetrahydroquinoxalin-2-yl)-acetamide (22 g, 0.11 mol) was dissolved in 10% NaOH (600 mL) and was heated under reflux for 3 hours. The mixture was cooled down via an ice-bath and was acidified with pre-cooled 10% HCl to pH˜6. The solvent was concentrated and the resulting precipitate was isolated via filtration to give a gray solid as the title product: 1H NMR (DMSO-d6) δ=12.35 (bs, 1H), 10.25 (bs, 1H), 6.74–6.68 (m, 3H), 6.61–6.58 (m, 1H), 5.91 (bs, 1H), 4.08–4.04 (m, 1H), 2.69 (dd, 1H, J=5.1, 16.2 Hz), 2.51 (dd, 1H, J=6.9, 16.2 Hz) was heated under reflux for 3 hours The mixture was cooled down via an ice-bath The solvent was concentrated the resulting precipitate was isolated via filtration

Conditions: temp:95.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of 1,2-phenylenediamine (21.5 g, 0.2 mol) in water (450 mL) was added dropwise a solution of maleimide, (20.0 g, 0.2 mol) in methanol (180 mL) over 60 min. The mixture was then stirred at 95° C. for 2 hours followed at rt overnight. The precipitate was collected via filtration and was washed with small amount of water for a few times to yield the title compound as a pale gray solid (pure product): 1H NMR (DMSO-d6) δ=10.2 (bs, 1H), 7.37 (bs, 1H) 6.88 (bs, 1H), 6.74–6.68 (m, 3H), 6.31–6.57 (m, 1H), 5.78 (bs, 1H), 4.08–4.04 (m, 1H), 2.63 (dd, 1H, J=3.6, 15.5 Hz), 2.32 (dd, 1H, J=3.3, 15.5 Hz); HPLC (CH3CN—H2O-0.1% TFA): Rf=9.49 min. followed at rt overnight The precipitate was collected via filtration was washed with small amount of water for a few times

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

Procedure: 2-(3-Oxo-1,2,3,4-tetrahydroquinoxalin-2-yl)-acetamide (22 g, 0.11 mol) was dissolved in 10% NaOH (600 mL) and was heated under reflux for 3 hours. The mixture was cooled down via an ice-bath and was acidified with pre-cooled 10% HCl to pH -6. The solvent was concentrated and the resulting precipitate was isolated via filtration to give a gray solid as the title product: 1H NMR (DMSO-d6) δ=12.35 (bs, 1H), 10.25 (bs, 1H), 6.74–6.68 (m, 3H), 6.61–6.58 (m, 1H), 5.91 (bs, 1H), 4.08–4.04 (m, 1H), 2.69 (dd, 1H, J=5.1, 16.2 Hz), 2.51 (dd, 1H, J=6.9, 16.2 Hz) was heated under reflux for 3 hours The mixture was cooled down via an ice-bath The solvent was concentrated the resulting precipitate was isolated via filtration