Pyridine → 3,4-Dihydroxy-5-nitrobenzaldehyde

Participants

Reaction Conditions

Reaction Steps

To a vigorously stirred suspension of 4-hydroxy-3-methoxy-5-nitrobenzaldehyde (47.0 g, 238 mmol) in EtOAc (450 mL) at room temperature, anhydrous aluminum chloride (38.1 g, 286 mmol) was added in one portion. Then pyridine (77 mL, 954 mmol) was added dropwise at 45-50° C. for 30 minutes. The reaction mixture was refluxed for 2 hours and allowed to cool down to 60° C. The reaction mixture was carefully poured into ice/concentrated HCl mixture (265 mL). After stirring at 50° C. for 1 hour, the reaction mixture was cooled to 0° C. The formed precipitate was separated by filtration, washed with water, and vacuum-dried to afford 3,4-dihydroxy-5-nitrobenzaldehyde (29.4 g, 161 mmol, 67.3% yield).

Provenance & Evidence