ethyl 5-cyano-1H-pyrrole-2-carboxylate

Conditions: temp:80.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To 260 mg of 5-cyano-1H-pyrrole-2-carboxylic acid ethyl ester (as prepared in the previous step) (1.59 mmol) in ethanol (6 mL) was added 1M aq sodium hydroxide (3.00 mL, 3.00 mmol) and the mixture was stirred at 80° C. for 2.5 h. The solvent was removed in vacuo, and the resulting solution was acidified to pH 3 with concentrated hydrochloric acid. The solid was collected on a filter and washed with water (1 mL) and dried under high vacuum to yield the title compound as a light tan solid which was used without further purification in the following step. The solvent was removed in vacuo The solid was collected on a filter washed with water (1 mL) dried under high vacuum

Conditions: temp:140.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A solution of 5-(hydroxyimino-methyl)-1H-pyrrole-2-carboxylic acid ethyl ester (as prepared in the previous step) (500 mg, 2.75 mmol) in acetic anhydride (5 mL) was stirred at 140° C. for 2 h. The cooled mixture was quenched with ice and then dichloromethane was added and the mixture was made basic with solid sodium bicarbonate. The layers were separated, the organic layer was washed with saturated sodium bicarbonate (2×10 mL), water (2×10 mL), then dried over Na2SO4. The solvent was removed in vacuo to yield 260 mg (58%) of the title compound as a light brown crystalline solid. 1H-NMR (400 MHz, CDCl3): δ 10.45 (br s, 1H), 6.89 (m, 1H), 6.83 (m, 1H), 4.42 (q, 2H, J=7.2 Hz), 1.40 (t, 3H, J=7.1 Hz). The cooled mixture was quenched with ice dichloromethane was added The layers were separated the organic layer was washed with saturated sodium bicarbonate (2×10 mL), water (2×10 mL) dried over Na2SO4 The solvent was removed in vacuo

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:80.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To 260 mg of 5-cyano-1H-pyrrole-2-carboxylic acid ethyl ester (as prepared in the previous step) (1.59 mmol) in ethanol (6 mL) was added 1M aq sodium hydroxide (3.00 mL, 3.00 mmol) and the mixture was stirred at 80° C. for 2.5 h. The solvent was removed in vacuo, and the resulting solution was acidified to pH 3 with concentrated hydrochloric acid. The solid was collected on a filter and washed with water (1 mL) and dried under high vacuum to yield the title compound as a light tan solid which was used without further purification in the following step. The solvent was removed in vacuo The solid was collected on a filter washed with water (1 mL) dried under high vacuum

Conditions: temp:140.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A solution of 5-(hydroxyimino-methyl)-1H-pyrrole-2-carboxylic acid ethyl ester (as prepared in the previous step) (500 mg, 2.75 mmol) in acetic anhydride (5 mL) was stirred at 140° C. for 2 h. The cooled mixture was quenched with ice and then dichloromethane was added and the mixture was made basic with solid sodium bicarbonate. The layers were separated, the organic layer was washed with saturated sodium bicarbonate (2×10 mL), water (2×10 mL), then dried over Na2SO4. The solvent was removed in vacuo to yield 260 mg (58%) of the title compound as a light brown crystalline solid. 1H-NMR (400 MHz, CDCl3): δ 10.45 (br s, 1H), 6.89 (m, 1H), 6.83 (m, 1H), 4.42 (q, 2H, J=7.2 Hz), 1.40 (t, 3H, J=7.1 Hz). The cooled mixture was quenched with ice dichloromethane was added The layers were separated the organic layer was washed with saturated sodium bicarbonate (2×10 mL), water (2×10 mL) dried over Na2SO4 The solvent was removed in vacuo

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:80.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To 260 mg of 5-cyano-1H-pyrrole-2-carboxylic acid ethyl ester (as prepared in the previous step) (1.59 mmol) in ethanol (6 mL) was added 1M aq sodium hydroxide (3.00 mL, 3.00 mmol) and the mixture was stirred at 80° C. for 2.5 h. The solvent was removed in vacuo, and the resulting solution was acidified to pH 3 with concentrated hydrochloric acid. The solid was collected on a filter and washed with water (1 mL) and dried under high vacuum to yield the title compound as a light tan solid which was used without further purification in the following step. The solvent was removed in vacuo The solid was collected on a filter washed with water (1 mL) dried under high vacuum

Conditions: temp:140.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A solution of 5-(hydroxyimino-methyl)-1H-pyrrole-2-carboxylic acid ethyl ester (as prepared in the previous step) (500 mg, 2.75 mmol) in acetic anhydride (5 mL) was stirred at 140° C. for 2 h. The cooled mixture was quenched with ice and then dichloromethane was added and the mixture was made basic with solid sodium bicarbonate. The layers were separated, the organic layer was washed with saturated sodium bicarbonate (2×10 mL), water (2×10 mL), then dried over Na2SO4. The solvent was removed in vacuo to yield 260 mg (58%) of the title compound as a light brown crystalline solid. 1H-NMR (400 MHz, CDCl3): δ 10.45 (br s, 1H), 6.89 (m, 1H), 6.83 (m, 1H), 4.42 (q, 2H, J=7.2 Hz), 1.40 (t, 3H, J=7.1 Hz). The cooled mixture was quenched with ice dichloromethane was added The layers were separated the organic layer was washed with saturated sodium bicarbonate (2×10 mL), water (2×10 mL) dried over Na2SO4 The solvent was removed in vacuo

Conditions: temp:0.00; pressure:0.00; stir: