HCID 57850033, compound → HCID 57850034, compound

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.

1. customHydrogenation was carried out at 37° C. in an oil bath under H2 atmosphere
2. customthe hydrogenation was continued further at 37° C. in an oil bath
3. waitAfter 22 h
4. filtrationthe mixture was filtered
5. customthe Pd catalyst separated
6. washwas washed with THF
7. washThe combined filtrate and washing
8. concentrationwere concentrated under reduced pressure
9. filtrationthe orange powder was collected by filtration
10. washwashed with H2O
11. customdried under vacuum

ORD record

ord-fb7126463afe45b0919a5835b106fb06

Source dataset

uspto-grants-2009_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07595400B2