Stannous chloride dihydrate → 7-(3,5-dimethyl-4-isoxazolyl)-6-(methoxy)-N4-(2-pyridinylmethyl)-3,4-quinolinediamine

Participants

Reaction Conditions

Reaction Steps

To a solution of this nitro intermediate (2.5 g, 24.82 mmol) in a mixture of ethanol (20 ml) and HCl (3.8 ml), was added portionwise SnCl2.2H2O (5.6 g, 24.82 mmol). The reaction mixture was heated to 40° C. for 1 h, then hydrolysed with sodium hydroxide N and extracted with DCM. The organic phase was washed with water, dried and concentrated to give the title compound as a brown powder (0.5 g, 17.8%). (APCI-MS) m/z: 376 MH+, Rt 2.46 min. 1H NMR (300 MHz, DMSO-d6, ppm) δ: 8.56 (d, 1H), 8.29 (s, 1H), 7.77 (dd, J=7.8, 7.6 Hz, 1H), 7.54 (s, 1H), 7.53-7.51 (m, 1H), 7.31-7.25 (m, 1H), 5.31 (s, 2H), 4.46 (d, J=7.2 Hz, 2H), 3.78 (s, 3H), 2.28 (s, 3H), 2.09 (s, 3H).

Provenance & Evidence