反応 #929945

反応方程式

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

反応条件

後処理

1. 1
   workup.ADDITIONAfter the addition
2. 2
   ろ過The resulting precipitate was filtered
3. 3
   その他chromatographed over silica gel
4. 4
   洗浄Elution with hexanes:ethyl acetate 90:10

実験手順

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.

出典