5-(Hydroxyimino-methyl)-1H-pyrrole-2-carboxylic acid ethyl ester → Ethyl 5-cyano-1H-pyrrole-2-carboxylate

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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).

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