Hydrazinium, 1,1,1-trimethyl-, iodide (1:1) → 2-Amino-4-cyano-3-hydroxynitrobenzene

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Reaction Steps

To a solution of 2-hydroxy-4-nitro-benzonitrile [1.0 g, 6.1 mmol, prepared as described in Yasubiro Imakura et. al. Chem. Pharm. Bull. 40 (7), 1691-1696 (1992)] in DMSO (60 mL) was added trimethylhydrazinium iodide (1.23 g, 6.09 mmol), followed by sodium tert-pentoxide (2.01 g, 6.09 mmol). The mixture was stirred at rt overnight, and then partitioned between 10% HCl and ether. The separated ether layer was washed with H2O, brine, dried (Na2SO4), and concentrated under reduced pressure to furnish the title compound (0.78 g) as a brown solid.

Provenance & Evidence