4-Nitro-N-propylbenzamide → 4-amino-N-propylbenzamide

Participants

Reaction Steps

A solution of 4-nitro-N-propylbenzamide (1.00 g, 4.80 mmoles) in MeOH (25 ml) was hydrogenated in the presence of a 5% palladium-on-charcoal catalyst at about 25° and atmospheric pressure. The catalyst was removed by filtration, and the filtrate was evaporated to dryness in vacuo to give 4-amino-N-propylbenzamide as a gummy residue; yiel 836 mg. This product was dissolved in DMAC (10 ml) containing I (504 mg, 1.50 mmoles), and the whole was stirred at room temperature for 72 hrs. The precipitate of the product was collected by filtration, washed with Et2O and dried in vacuo over P2O5 ; yield 74% (482 mg), mp > 340° (Mel-Temp). This sample was homogeneous on tlc (5:1 CHCl3 -MeOH). Anal. Calcd for C17H20N8O.HBr: C, 47.12; H, 4.88; N, 25.86. Found: C, 47.10; H, 5.18; N, 25.55. Spectral data: λ max, nm (ε × 10-3), 0.1 N HCl, 244 (18.5), 284 (18.3), 337 (10.5), 345 (sh) (9.70); pH 7, 261 (26.9). 279 (24.2), 371 (7.65); 0.1 N NaOH, 261 (27.1), 279 (24.2), 371 (7.73); δ 0.96 (t, 3, CH3), 1.50 (m, 2, CH2CH3), 3.17 (m, 2, NHCH2CH2), 4.62 (s, 2, CH2N), 7.23 (m, 4, C6H4), 8.07 (m, 1, NHCO), 8.87 (s, 1, C7 --H), 9.35 (NH). Some of the NH2 peaks were too broad to locate but are observed in the integral.

Provenance & Evidence