4-Aminobenzyl alcohol → (4-((4-((3-Azidopropyl)(methyl)amino)-2-methoxyphenyl)diazenyl)phenyl)methanol

Participants

Reaction Conditions

Reaction Steps

4-aminobenzylalcohol (0.275 g, 2.24 mmol) and NaNO2 (0.16 g, 2.35 mmol) were dissolved in EtOH/water (4.5+3.0 mL=7.5 mL), to which 2 N HCl solution (4.5 mL) was added at 0° C. and reaction mixture stirred at 0° C. for 1 hour. Compound 17 (0.45 g, 2.04 mmol) in EtOH was added followed by addition of NaOAc (0.15 g) at 0° C. and mixture stirred for 6 hours at room temperature. The remaining procedure was followed as described for compound 1 to obtain compound 19. Yield: 0.58 g (81%). 1H NMR (500 MHz, CDCl3): δ 1.87 (tt, 2H, J=6.5, 13.0 Hz, Hc), 2.31 (bs, 1H, OH), 3.03 (s, 3H, NCH3, Ha), 3.36 (tt, 2H, J=3.0 & 6.5 Hz, Hd), 3.49 (tt, 2H, J=3.0 & 7.5 Hz, Hb), 4.00 (s, 3H, OMe), 4.67 (s, 2H, Hj), 6.20-6.25 (m, 1H, Hg), 6.30-6.33 (m, 1H, He), 7.35-7.42 (m, 2H, Hi), 7.70-7.80 (m, 3H, Hh, Hf); 13C NMR (125 MHz, CDCl3): δ 26.46 (Cc), 38.62 (Ca), 48.82 (Cd), 49.45 (Cb), 55.20 (OCH3), 64.77 (Cj), 94.94 (Cg), 104.65 (Ce), 118.18 (Cf), 122.33 (Ci), 127.29 (Ch), 133.54 (Cl), 141.85 (Cn), 152.85 (Cm), 152.91 (Ck), 159.19 (Co). EI-MS: [M+H]+ C18H23N6O2 calcd 355.18, obsd 355.16.

Provenance & Evidence