تفاعل #1193290

معادلة التفاعل

sodium

4-aminobenzamidine 2HCl

diethyl ethoxymethylenemalonate

→

title compound

2-(4-Aminophenyl)-4-hydroxy-5-pyrimidine carboxylic acid

المذيبات

ethanol

ظروف التفاعل

المعالجة

1. 1
   workup.STIRRINGAfter stirring for 30 min
2. 2
   درجة الحرارةthe mixture is refluxed for 4 hr
3. 3
   workup.WAITto stand overnight at room temperature
4. 4
   ترشيحThe salt is filtered
5. 5
   غسيلwashed with isopropanol
6. 6
   workup.STIRRINGstirred at 70° C. for 4 hr
7. 7
   workup.ADDITIONAfter treating with a small amount of charcoal
8. 8
   workup.ADDITIONthe filtrate is added to 325 ml of 2 N HCl
9. 9
   workup.STIRRINGwith stirring
10. 10
    ترشيحThe acid is filtered
11. 11
    غسيلwashed with water, ethanol, and ether
12. 12
    أخرىdried

الإجراء التجريبي

A solution of 14.8 g (0.642 mmol) of sodium in 750 ml of dry ethanol is stirred at 0° and 44.6 g (0.214 mmol) of 4-aminobenzamidine 2HCl [Shaw and Cooley, J. Am. Chem. Soc., 79, 3561 (1957)] is added. The mixture is stirred 5 minutes under nitrogen and 46.2 g (0.214 mmol) of diethyl ethoxymethylenemalonate is added. After stirring for 30 min, the mixture is refluxed for 4 hr and allowed to stand overnight at room temperature. The salt is filtered and washed with isopropanol. The salt is suspended in 214 ml of 2 N potassium hydroxide and stirred at 70° C. for 4 hr. After treating with a small amount of charcoal, the filtrate is added to 325 ml of 2 N HCl with stirring. The acid is filtered, washed with water, ethanol, and ether, and dried to give 50.8 g of the title compound, mp 312°-314° C. dec. The product is recrystallized from dimethylacetamide-water to give 44.5 g mp 313°-314° C. dec. ##EQU42##

المصدر