Stannous chloride dihydrate → 5-amino-N,N-diethyl-6-(2-propenylamino)-3-pyridinecarboxamide

Participants

Reaction Conditions

Reaction Steps

To a solution of N,N-diethyl-5-nitro-6-(2-propenylamino)-3-pyridinecarboxamide (4.83 g, 17.25 mmol) in DMF (50 mL) at room temperature was added tin dichloride dihydrate (8.56 g, 37.95 mmol). The mixture was stirred overnight at 80° C. The reaction was brought to room temperature and concentrated in vacuo. The residue was taken up into NaHCO3 saturated aqueous solution (100 mL) and EtOAc (100 mL). The suspension was filtered and the phases separated. The aqueous phase was back-extracted with additional EtOAc (100 mL). The organic phases were combined, dried with MgSO4, filtered and concentrated in vacuo. The residue was purified using silica gel flash chromatography ([5% MeOH+1% NH4OH aq] in CH2Cl2) to provide 2.10 g of the title compound 5-amino-N,N-diethyl-6-(2-propenylamino)-3-pyridinecarboxamide (49.0% yield from N,N-diethyl-5-nitro-6-(2-propenylamino)-3-pyridinecarboxamide). 1H-NMR (400 MHz, CDCl3): δ 1.20 (t, J=7.2 Hz, 6H), 3.23 (br s, 1H), 3.45 (m,4H), 4.12 (m, 2H), 4.44 (br s, 2H), 5.17 (d, J=12.5 Hz, 1H), 5.26 (d, J=17.2 Hz, 1H), 6.04 (m, 1H), 7.00 (d, J=2.0 Hz, 1H), 7.83 (d, J=2.0 Hz, 1H). MS (ESI) (M+H)+: 2.49.

Provenance & Evidence