Hydroxylamine → HCID 9816024, compound

Participants

Reaction Steps

Finely ground Cd/Pb couple (1.02 g). was added in small portions to a stirred solution of 100 (0.64 g, 1.51 mmol) in THF (10 mL) and 1M NH2OAc (10 mL). The reaction was followed by TLC (EtOAc), when no more starting material was observed, the mixture was poured into ethyl acetate (200 mL). The organic phase was dried over MgSO4 and evaporated to yield the product as a pale yellow oil (0.28 g, 80%): 1H NMR (270 MHz, CDCl3) δ 2.15 (m, 4H); 3.52 (m, 2H); 3.87 (s, 3H); 5.15 (m, 1H); 6.8-7.2 (m, 3H); 7.8 (d, J=4.7 Hz, 1H, imine H11). IR (Nujol): cm−1 3373, 2975, 1621, 1576, 1440, 1419, 1250, 1075, 750. MS: m/e (relative intensity) 230 (M+., 100), 215 (45), 201 (20), 187 (5), 160 (5), 146 (4), 133 (20), 105 (10), 76 (25), 70 (45), 63 (3), 51 (3). HRMS Calculated for C13H14N2O2: 230.1055. Found: 230.1055. [α]25D=+455.3° (c=0.6, CHCl3).

Provenance & Evidence