Reaktion #492953

Reaktionsgleichung

3-(imidazo[1,2-a]pyridine-3-carboxamido)-4-methylbenzoate

LiOH

water

→

3-(imidazo[1,2-a]pyridine-3-carboxamido)-4-methylbenzoic acid

Lösungsmittel

THF

MeOH

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigeto remove THF and MeOH
2. 2
   workup.ADDITIONThe mixture was diluted with water (75 mL)
3. 3
   FiltrationThe resulting precipitate was filtered
4. 4
   Waschenwashed with water
5. 5
   Sonstigedried under vacuum

Vorschrift

To a suspension of 3-(imidazo[1,2-a]pyridine-3-carboxamido)-4-methylbenzoate (3) (5.43 g, 17.6 mmol) in THF (225 ml) and MeOH (150 mL) was added LiOH 3 M (17.5 mL) and water (50 mL). The reaction was stirred at room temperature for 12 hours then reduced in volume on roto-vap to remove THF and MeOH. The mixture was diluted with water (75 mL) and neutralized with HCl (17.5 mL of a 3M solution). The resulting precipitate was filtered, washed with water and dried under vacuum to afford 3-(imidazo[1,2-a]pyridine-3-carboxamido)-4-methylbenzoic acid (4) as a white solid. 1H NMR (400 MHz, d6-DMSO) δ 10.0 (s, 1H), 9.45 (dt, J=6.8, 1.2 Hz, 1H), 8.58 (s, 1H), 7.98 (d, J=2.0 Hz, 1H), 7.79 (dt, J=9.2, 1.2 Hz, 1H), 7.76 (dd, J=8.0, 1.6 Hz, 1H), 7.52 (ddd, J=9.2, 9.2, 1.2 Hz, 1H), 7.43 (d, J=8.0 Hz, 1H), 7.17 (td, J=6.8, 1.2 Hz, 1H), 2.35 (s, 3H). MS m/z 296.1 (M+1)+.

Quelle