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

HRID 1679126Notes

Reaction equation

HRID 1679126 reaction equation
[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

Participants

4

Reactant 1

HCID 3146644-Nitro-N-propylbenzamide

Product 1

HCID 4283444-amino-N-propylbenzamideYield 74%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

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.

Workup

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

Sources & evidence

ORD record
ord-ffeca2f26a6245b4b91dc23a02588d4a
Source dataset
uspto-grants-1978_03
Patent number
US04079056

Reaction notes

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