Reacción #3235

Ecuación de reacción

7-chloro-2,3-dihydro-10-hydrazinopyridazino[4,5-b]quinoline-1,4-dione hydrochloride

7-Chloro-2,3-dihydro-10-hydrazinopyridazino[4,5-b]quinoline-1,4-dione hydrochloride

beta alanine ethyl ester hydrochloride

→

ester

Rendimiento 13.0%

10-(2-Ethoxycarbonylethylamino)-7-chloro-2,3-dihydropyridazino[4,5-b]quinoline-1,4-dione

Rendimiento 13.0%

Disolventes

water

pyridine

Condiciones de reacción

Tratamiento posterior

1. 1
   Temperaturawas refluxed for 23 hr
2. 2
   TemperaturaAfter cooling
3. 3
   Otrothe vigorously stirred reaction mixture
4. 4
   Filtraciónfiltered
5. 5
   Otroto separate a fine red solid
6. 6
   LavadoThe collected solids were washed with water
7. 7
   Otrochromatographed (eluant: methanol/methylene chloride; 5/95) over silica gel

Procedimiento

A mixture of 7-chloro-2,3-dihydro-10-hydrazinopyridazino[4,5-b]quinoline-1,4-dione hydrochloride (1.0 g, 2.9 mM, as prepared in Example 44) and beta alanine ethyl ester hydrochloride (49.0 g, 320 mM) in pyridine (52 mL) was refluxed for 23 hr. After cooling, the vigorously stirred reaction mixture was diluted slowly with water (100mL) and then filtered to separate a fine red solid. The collected solids were washed with water and chromatographed (eluant: methanol/methylene chloride; 5/95) over silica gel to provide the title ester (0.13 g, 13%) as a red powder, mp 258°-260° C.; MS(CI): 363 (M+H).

Fuente