2-Nitroacetamide → 6-Cyclopropyl-3-nitropyridin-2-ol

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Reaction Steps

A mixture of crude β-N,N-dimethylaminoethenylcyclopropyl ketone (12 g, <86 mmol), nitroacetamide (9 g, 86 mmol) and aqueous piperidinium acetate (10 ml) [prepared from glacial acetic acid (42 ml), water (100 ml) and piperidine (72 ml)] was stirred at room temperature overnight. Following dilution with water (20 ml), the yellow precipitate was isolated via filtration and drying in vacuo to yield 5.30 g of the title compound: 1H NMR (CDCl3) δ1.15 (m, 2 H), 1.36 (m, 2 H), 2.10 (m, 1 H), 6.02 (br d, J=8.0Hz, 1 H), 8.41 (d, J=8.0 Hz, 1 H).

Provenance & Evidence