4-chloro-1-N-methylbenzene-1,2-diamine

Conditions: temp:150.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 4-chloro-N1-methylbenzene-1,2-diamine (15.0 g, 96 mmol) and glycolic acid (8.1 g, 106 mmol) were mixed together in a sealed tube. The mixture was heated at 150° C. for 5 hours before it was cooled down to room temperature. The residue was purified by flash column chromatography (0–5% MeOH in CH2Cl2) to give the product (8.5 g, 45% yield). 1H NMR (300 MHz, CDCl3) δ: 3.80 (s, 3 H), 4.86 (s, 2 H), 7.13–7.22 (m, 2 H), 7.62–7.64 (m, 1 H). was cooled down to room temperature The residue was purified by flash column chromatography (0–5% MeOH in CH2Cl2)

Conditions: temp:50.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of 4-chloro-N-methyl-2-nitroaniline (713 mg, 3.8 mmol) in ethanol (10 mL) is added ammonium formate (1.2 g, 19 mmol) followed by zinc dust (745 mg, 11.5 mmol). The reaction is heated to 50° C. for 2 h. The room temperature suspension is filtered through a bed of Celite and the filtrate is rinsed with additional methanol (10 mL). The filtrate is concentrated to afford the title compound (592 mg, 89%) as an oil which was used in the next step without purification The room temperature suspension is filtered through a bed of Celite the filtrate is rinsed with additional methanol (10 mL) The filtrate is concentrated

Conditions: temp:150.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 4-chloro-N1-methylbenzene-1,2-diamine (15.0 g, 96 mmol) and glycolic acid (8.1 g, 106 mmol) were mixed together in a sealed tube. The mixture was heated at 150° C. for 5 hours before it was cooled down to room temperature. The residue was purified by flash column chromatography (0-5% MeOH in CH2Cl2) to give the product (8.5 g, 45% yield). 1H NMR (300 MHz, CDCl3) δ: 3.80 (s, 3H), 4.86 (s, 2H), 7.13-7.22 (m, 2H), 7.62-7.64 (m, 1H). was cooled down to room temperature The residue was purified by flash column chromatography (0-5% MeOH in CH2Cl2)

Conditions: temp:150.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 4-chloro-N1-methylbenzene-1,2-diamine (15.0 g, 96 mmol) and glycolic acid (8.1 g, 106 mmol) were mixed together in a sealed tube. The mixture was heated at 150° C. for 5 hours before it was cooled down to room temperature. The residue was purified by flash column chromatography (0–5% MeOH in CH2Cl2) to give the product (8.5 g, 45% yield). 1H NMR (300 MHz, CDCl3) δ: 3.80 (s, 3 H), 4.86 (s, 2 H), 7.13–7.22 (m, 2 H), 7.62–7.64 (m, 1 H). was cooled down to room temperature The residue was purified by flash column chromatography (0–5% MeOH in CH2Cl2)