HCID 899189, compound → 856047-84-2

Participants

Reaction Steps

2-(Diethylamino)-N-(3-nitrophenyl)acetamide 4 (0.73 g, 2.90 mmol) was dissolved in anhydrous THF (20 ml) under an atmosphere of N2, then Pd/C (0.073 g) was added. The atmosphere was then saturated with H2 and the mixture stirred overnight. The crude product was filtered through celite, the celite washed with EtOAc and the organic solution evaporated in vacuo. The crude was dissolved in DCM (75 ml), washed 3 times with 5N aqueous NH4OH solution (50 ml), dried (MgSO4), filtered and the solvent evaporated in vacuo. Compound N-(3-aminophenyl)-2-(diethylamino)acetamide 5 was obtained as a yellow oil (0.58 g, 90%) without requiring any further purification; Rf 0.44 [5% MeOH in DCM]; δH (CDCl3, 400 MHz) 9.28 (1H, s, NH), 7.26-7.20 (1H, m, ArH), 7.07 (1H, t, J=8.0 Hz, ArH), 6.74-6.72 (1H, m, ArH), 6.43-6.40 (1H, m, ArH), 3.71 (2H, broad s, NH2), 3.11 (2H, s, CH2), 2.65-2.59 (4H, m, 2×CH2), 1.69 (6H, t, J=7.2 Hz, 2×CH3); δC (CDCl3, 100 MHz) 169.95 (C═O), 147.27 (Ar—C), 138.64 (Ar—C), 129.61 (Ar—CH), 110.74 (Ar—CH), 109.17 (Ar—CH), 105.92 (Ar—CH), 58.14 (CH2), 48.79 (2×CH2), 12.39 (2×CH3); HRMS m/z calc. C12H20N3O [M+H]+222.1601. found [M+H]+ 222.1694.

Provenance & Evidence