Potassium Carbonate → 3-Pyridinecarboxaldehyde, 2-amino-

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Reaction Steps

Crude 2-(pivaloylamino)-3-pyridinecarboxaldehyde (from step b, 43 g) was dissolved in 3 M HCl (500 mL), and the solution was heated to reflux. After 18 hr the mixture was cooled to RT, and the pH was carefully adjusted to 7 using solid K2CO3. The aqueous solution was extracted with EtOAc (3×500 mL). The combined organic layers were dried (MgSO4)and concentrated to give the title compound (24.57 g, 101%) as a reddish brown solid: 1H NMR (300 MHz, CDCl3) δ 9.85 (s, 1H), 8.24 (m. 1 H), 7.80 (m, 1H), 6.90 (br s, 2H), 6.74 (m, 2H); MS (ES) m/e 123 (M+H)+.

Provenance & Evidence