Sodium Iodide → 2-Hydroxy-4-iodonicotinaldehyde

Participants

Reaction Steps

4-Iodo-2-methoxynicotinaldehyde (25 g, 83 mmol, prepared according to WO95/29917) and sodium iodide (37.0 g, 249 mmol) were combined in MeCN (500 mL). Chlorotrimethylsilane (31.4 mL, 249 mmol) was added dropwise over 15 min. The reaction mixture was stirred at RT for 2 h and then concentrated under vacuum. The crude product was suspended in a mixture of EtOAc, water, and saturated aqueous NaHCO3, then filtered to give a dark brown solid. This solid was triturated with MeCN to yield 4-iodo-2-oxo-1,2-dihydropyridine-3-carbaldehyde (12 g, yield 50.5%) as a yellow solid. MS (ESI) m/z: 250.0 (M+H+).

Provenance & Evidence