Réaction #46536

Équation de réaction

tert-butyl (E)-3-(7-oxo-5,6,7,8-tetrahydro-1,8-naphthyridin-3-yl)acrylate

TFA CH2Cl2

→

title compound

Rendement 100.0%

(E)-3-(7-oxo-5,6,7,8-tetrahydro-1,8-naphthyridin-3-yl)acrylic acid hydrochloride salt

Rendement 100.0%

Conditions de réaction

Traitement

1. 1
   Concentrationwas concentrated under vacuum
2. 2
   Autretriturated
3. 3
   Concentrationconcentrated to dryness
4. 4
   AutreThe resulting solid was triturated with Et2O
5. 5
   Autrecollected
6. 6
   Autredried under vacuum

Mode opératoire

To tert-butyl (E)-3-(7-oxo-5,6,7,8-tetrahydro-1,8-naphthyridin-3-yl)acrylate (7.0 g, 25.5 mmole) was added 1:1 TFA/CH2Cl2 (100 mL). The reaction was stirred for 30 min, then was concentrated under vacuum. The residue was suspended in 4 N HCl/dioxane (100 mL), triturated, and concentrated to dryness. The resulting solid was triturated with Et2O, collected, and dried under vacuum to give the title compound (6.55 g, 100%) as a off-white solid: 1H NMR (400 MHz, d6-DMSO) δ 10.72 (s, 1 H), 8.35 (d, J=2.0 Hz, 1 H), 8.04 (s, 1H), 7.54 (d, J=16.0 Hz, 1 H), 6.51 (d, J=16.0 Hz, 1 H), 2.91 (t, 2 H), 2.53 (t, 2 H); MS (ES) m/e 219.0 (M+H)+.

Source