HCID 57850033, compound → HCID 57850034, compound

Participants

Reaction Steps

N-(2-Formyl-3-nitrophenyl)formamide (5a, 51.6 g, 0.27 mol) was dissolved in THF (1 L) and 20 wt % Pd(OH)2 on activated charcoal (4.96 g) was added. Hydrogenation was carried out at 37° C. in an oil bath under H2 atmosphere. After being stirred for 4 h, an additional 20 wt % Pd(OH)2 on activated charcoal (2.01 g) was added and the hydrogenation was continued further at 37° C. in an oil bath. After 22 h, the mixture was filtered and the Pd catalyst separated was washed with THF. The combined filtrate and washing were concentrated under reduced pressure. The generated crude solid was suspended in H2O (500 mL) and then the orange powder was collected by filtration, washed with H2O, and dried under vacuum to obtain N-(3-amino-2-formylphenyl)-formamide (7a, 40.2 g, 92%); 1H NMR (270 MHz) δ (CD3OD): rotamer A (major)* 6.53 (d, J=7.9 Hz, 1H), 6.66 (d, J=7.9 Hz, 1H), 7.17 (t, J=7.9 Hz, 1H), 8.23 (s, 1H), 9.97 (s, 1H); rotamer B (minor)* 6.33 (d, J=7.9 Hz, 1H), 6.54 (d, J=7.9 Hz, 1H), 7.17 (t, J=7.9 Hz, 1H), 8.40 (s, 1H), 10.05 (s, 1H). The ratio of two rotamers A and B is approximately 2:1.

Provenance & Evidence