Sodium Carbonate → Ethyl 6-(methoxy(methyl)amino)-4-(methylamino)nicotinate

Participants

Reaction Conditions

Reaction Steps

A mixture of ethyl 6-chloro-4-(methylamino)nicotinate (8 g, 37.4 mmol) and O,N-dimethylhydroxylamine hydrochloride (91 g, 0.94 mol) in dioxane (10 mL) was heated to 180° C. for 6 h. The reaction mixture was cooled to RT, and saturated aq Na2CO3 solution was added until pH 7. The aqueous solution was extracted with EtOAc (3×100 mL). The combined organics were washed with brine, dried (MgSO4) and concentrated in vacuo to give ethyl 6-(methoxy(methyl)amino)-4-(methylamino)nicotinate (6.6 g, 74% yield), which was used in the next step without further purification. 1HNMR (400 MHz, DMSO-d6): δ 8.44 (s, 1 H), 7.82 (m, 1H), 6.05 (s, 1 H), 4.20 (q, J=7.2 Hz, 2 H), 3.67 (s, 3 H), 3.17 (s, 3 H), 2.82 (d, J=5.2 Hz, 3 H), 1.25 (t, J=7.2 Hz, 3 H), MS (ESI) m/z: 240.1 (M+H+)

Provenance & Evidence