Reacción #1563897

Ecuación de reacción

2,2-Dimethyl-[1,3]dioxane-4,6-dione

Meldrum's acid

2-isopropylaminobenzaldehyde

acetic acid

ethylenediamine

→

1-isopropyl-2-oxo-1,2-dihydroquinoline-3-carboxylic acid

Rendimiento 98.0%

Disolventes

methanol

Condiciones de reacción

Tratamiento posterior

1. 1
   Otroat room temperature
2. 2
   Otroovernight
3. 3
   FiltraciónThe resulting suspension was filtered
4. 4
   Lavadothe solid washed with methanol
5. 5
   Otrocollected

Procedimiento

2,2-Dimethyl-[1,3]dioxane-4,6-dione, commonly Meldrum's acid, (166.9 g, 1.16 mol) was added to a stirred solution of 2-isopropylaminobenzaldehyde (105 g, 0.64 mol), acetic acid (73.6 mL, 1.29 mol) and ethylenediamine (43.0 mL, 0.64 mol) in methanol (1 L) at 0° C. The reaction mixture was stirred for 1 h at 0° C. and then at room temperature overnight. The resulting suspension was filtered and the solid washed with methanol and collected to yield the title intermediate, 1-isopropyl-2-oxo-1,2-dihydroquinoline-3-carboxylic acid (146 g, 98%) as an off-white solid. 1H NMR (CDCl3; 300 MHz): 1.72 (d, 6H, CH(CH3)2), 5.50 (bs, 1H, CH(CH3)2), 7.44 (t, 1H, ArH), 7.75-7.77 (m, 2H, ArH), 7.82 (d, 1H, ArH), 8.89 (s, 1H, CH).

Fuente