Reacción #929945

Ecuación de reacción

sodium borohydride

acetic acid

8-amino-5-(3,4-dichlorophenoxy)-6-methoxy-4-methylquinoline

4-oxo-1-phthalimidopentane

sodium hydroxide

→

expected product

5-(3,4-dichlorophenoxy)-6-methoxy-1methyl-8-[(4-phthalimido-1-methylbutyl)amino]quinoline

5-(3,4-dichlorophenoxy)-6-methoxy-4-methyl-8-[(4-phthalimido-1-methylbutyl)amino]quino line

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.ADDITIONAfter the addition
2. 2
   FiltraciónThe resulting precipitate was filtered
3. 3
   Otrochromatographed over silica gel
4. 4
   LavadoElution with hexanes:ethyl acetate 90:10

Procedimiento

A mixture of 12.4 g of 8-amino-5-(3,4-dichlorophenoxy)-6-methoxy-4-methylquinoline (36 mM) and 11.6 g of 4-oxo-1-phthalimidopentane (50 mM), in glacial acetic acid was stirred for 15 min under nitrogen and 2.6 g of sodium borohydride (70 mM) was added portionwise maintaining the temperature 25-35° C. After the addition, the reaction mixture was stirred for 30 min and then poured into ice cold solution of concentrated sodium hydroxide. The resulting precipitate was filtered and chromatographed over silica gel. Elution with hexanes:ethyl acetate 90:10 yielded the expected product of 5-(3,4-dichlorophenoxy)-6-methoxy-4-methyl-8-[(4-phthalimido-1-methylbutyl)amino]quino line which was crystallized from ether to give 12.4 g (22 mM) of yellow crystalline product.

Fuente