Hydrochloric Acid → 1H-Pyrrolo[2,3-b]pyridine-3-carbonitrile, 1-(1,1-dimethylethyl)-5-nitro-

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Reaction Steps

To a solution of 5.85 g (35.8 mmol) of 5-amino-1-tert-butyl-1H-pyrrole-3-carbonitrile, being prepared as disclosed in Org. Proc. Res. Dev., 7(2), 209-213, 2003, in 120 mL of n-propanol, it was added sodium nitromalonaldehyde (6.02 g, 43.0 mmol) portionwise under stirring at room temperature. The resulting mixture was treated dropwise with 37% hydrochloric acid (4.6 mL, 55.2 mmol) and heated at 100° C. for 2 hours. The reaction mass was concentrated under vacuum to ⅓ of the initial volume and kept at 4° C. for 18 hours. The precipitate was filtered off, washed thoroughly with 15% aqueous ethanol (35 mL), water (5 mL) and finally dried to afford 7.14 g of the title compound as a light brown solid.

Provenance & Evidence