Sodium Hydroxide → 6-[(Tert-butoxy)carbonyl]pyridine-3-carboxylic acid

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Reaction Steps

A mixture of methyl 6-tert-butoxycarbonylnicotinate (1.2 g, 5.06 mmol) in THF (15 ml) and 0.25 N NaOH (40 ml, 10 mol) at an ambient temperature for 0.5 hr. The mixture was poured into ice-1N HCl (10 ml). The solid was collected, washed with water and air-died. The crude solid was recrystallized from CHCl3—EtOH—IPE to afford 6-tert-butoxycarbonylnicotinic acid (850 mg, 76%) as needles. IR (KBr) m/n 3095, 1728, 1705 cm−1; 1H-NMR (DMAO-d6) δ1.63 (s, 9 H), 8.09 (m, 1 H), 8.17 (m, 1 H), 8.42 (dt, J=2.4 and 8.3 Hz, 1 H), 9.21 (t, J=2.4 and 8.8 Hz, 1 H); MS (FAB) m/z 224 (M++1); Anal. Calcd. for C29H33N3O6: C, 36.18; H,3.18; N, 3.84. Found: C, 36.85; H, 3.35; N, 3.79.

Provenance & Evidence