Formaldehyde → HCID 18353752, compound

Participants

Reaction Steps

2-[3-(3,4-Dichlorobenzylamino)prop-1-ylamino]-1H-quinolin-4-one (0.026 g, 0.07 mmol) was dissolved in methanol (2 ml) and acetic acid (0.05 ml). This was cooled in an ice bath and treated sequentially with sodium cyanoborohydride (6.3 mg, 0.1 mmol) in methanol (0.4 ml) and formaldehyde (3.7% in water/methanol, 0.057 ml, 0.07 mmol) then stirred for 4 h. The reaction mixture was purified by chromatography on a SCX cartridge, eluting with methanol and then 0.2M NH3 in methanol to give the title compound as a pale pink solid (0.027 g, 99%); δH (CD3OD) 1.7-1.9 (2H, m), 2.16 (3H, s), 2.43 (2H, t), 3.25-3.35 (2H, m), 3.43 (2H, s), 5.57 (1H, s), 7.1-7.6 (6H, m), and 8.03 (1H, d); MS (ES+) 390, 392 (45, 30%, MH+) and 201 (100).

Provenance & Evidence