Triphenylphosphine → 2-Amino-4-((4-nitronaphthalen-1-yloxy)methyl)pyridine

Participants

Reaction Steps

To a solution of 4-nitronaphthol (5.17 g, 27.3 mmol), triphenylphosphine (10.75 g, 41.0 mmol) and 2-aminopyridine-4-methanol (5.09 g, 41.0 mmol) in THF (50 mL) at −15° C. was added dropwise DIAD (8.07 mL, 41.0 mmol) and the mixture then allowed to warm to RT and stirred overnight. The volatiles were removed in vacuo and the residue was triturated with EtOAc (150 mL), and the crude product was collected by filtration and washed with EtOAc (100 mL). A second trituration with MeOH (100 mL) gave 2-amino-4-((4-nitronaphthalen-1-yloxy)methyl)pyridine (4.54 g, 56%) as a yellow solid: m/z 296 (M+H)+ (ES+).

Provenance & Evidence