Réaction #323005

Équation de réaction

water

4-methoxybenzoic acid

isopropyl ether

2-amino-7-isopropoxy-1,8-naphthyridine

→

N-(7-isopropoxy-1,8-naphthyridin-2-yl)-4-methoxybenzamide

Rendement 34.8%

Solvants

diethyl ether

Conditions de réaction

Traitement

1. 1
   Extractionextracted with ethyl acetate
2. 2
   ConcentrationAfter concentration to dryness under reduced pressure (4 kPa)
3. 3
   Autrethe oil produced (39 g)
4. 4
   Autreto give a crystallised solid (23 g; m.p. 78° C.)
5. 5
   AutreThe product produced
6. 6
   workup.DISSOLUTIONis dissolved
7. 7
   Autrethe crystallised solid is separated by filtration
8. 8
   Lavagewashed with diethyl ether (2×10 cc)
9. 9
   Autredried at 40° C. under reduced pressure (0.067 kPa)

Mode opératoire

The procedure is similar to that described in Example 1, but starting with 4-methoxybenzoic acid (16.7 g), N,N'-carbonyldiimidazole (19.4 g) and 2-amino-7-isopropoxy-1,8-naphthyridine (25 g). The reaction mixture is poured into water and extracted with ethyl acetate. After concentration to dryness under reduced pressure (4 kPa), the oil produced (39 g) is stirred in the presence of diethyl ether (100 cc) to give a crystallised solid (23 g; m.p. 78° C.). The product produced is dissolved in boiling isopropyl ether (100 cc). After 2 hours' cooling at 4° C., the crystallised solid is separated by filtration, washed with diethyl ether (2×10 cc) and dried at 40° C. under reduced pressure (0.067 kPa). N-(7-isopropoxy-1,8-naphthyridin-2-yl)-4-methoxybenzamide (12.9 g) is produced, m.p. 82° C.

Source