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

Participants

Reaction Steps

A solution of 2-Amino-4-[(4-nitronaphthalen-1-yloxy)methyl]pyridine (3) (4.50 g, 15.24 mmol) in methanol (200 mL) and glacial acetic acid (200 mL) was passed through a Thales ‘H-cube’ flow reactor (2 mL min−1, 40° C., 55 mm 10% Pt/C Cat-Cart®, full H2) and the volatiles were then removed in vacuo. The crude product was subjected to SCX capture and release eluting with 1% ammonia in MeOH solution and the solvent was removed in vacuo to give 2-amino-4-[(4-aminonaphthalen-1-yloxy)methyl]pyridine (4) (3.82 g, 94%) as a mauve solid: m/z 266 (M+H)+ (ES+).

Provenance & Evidence