Sodium Hydroxide → 5-Nitro-2-thiophenecarboxaldehyde oxime

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A mixture of 5-nitrothiophene-2-carboxaldehyde (10 g, 64 mmol), hydroxylamine hydrochloride (9.4 g, 130 mmol) and sodium hydroxide (4.34 g, 107 mmol) in ethanol/water (150 ml, 2:1) was heated to reflux for 2 hours, then diluted with dichloromethane and washed with water. The organic layer was dried over magnesium sulfate and evaporated to dryness to give 8.8 g of 5-nitro-2-thiophene-carboxaldehyde oxime as a tan solid. 1H NMR (400 MHz, DMSO-d6) δ: 7.54 (1H, d), 8.13 (1H, s), 8.16 (1H, d), 13.14 (1H, s).

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