Aniline → 5-Cyano-2-(2-phenylchroman-6-yloxy)-aniline

Participants

Reaction Steps

4-Cyano-2-nitro-1-(2-phenylchroman-6-yloxy)-benzene (0.155 g; 0.4 mmol) was reduced to the corresponding aniline as described for 2-(2-phenylchroman-6-yloxy)-aniline in Example 29 except that 40 ml of glacial acetic acid and 0.93 g of zinc powder were used. Product was purified by column chromatography (100% CH2Cl2 as the eluant). 1H-NMR (300 MHz; d6-DMSO): δ 7.57-7.28 (m, 5H), 7.06 (d, 1H, J=2.0 Hz), 6.95-6.78 (m, 4H), 6.65 (d, 1H, J=8.3 Hz), 5.46 (s, 2H), 5.11 (dd, 1H, J=10.0 Hz, J=2.1 Hz), 3.03-2.88 (m, 1H), 2.78-2.66 (m, 1H), 2.23-2.10 (m, 1H), 2.08-1.89 (m, 1H).

Provenance & Evidence