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

HRID 1678866Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1678866
[N+:1]([C:4]1[CH:15]=[CH:14][C:7]([C:8]([NH:10][CH2:11][CH2:12][CH3:13])=[O:9])=[CH:6][CH:5]=1)([O-])=O>CO.[Pd]>[NH2:1][C:4]1[CH:5]=[CH:6][C:7]([C:8]([NH:10][CH2:11][CH2:12][CH3:13])=[O:9])=[CH:14][CH:15]=1

Komponenten

4

Edukt 1

HCID 3146644-Nitro-N-propylbenzamide

Produkt 1

HCID 4283444-amino-N-propylbenzamideAusbeute 74 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 887MethanolLösungsmittel

Versuchsvorschrift

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: λmax, 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); β 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.

Aufarbeitung

  1. customThe catalyst was removed by filtration
  2. customthe filtrate was evaporated to dryness in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-a68e067909174812abbe68710af9a621
Quelldatensatz
uspto-grants-1978_03
Patentnummer
US04077957

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