반응 #353296

반응 방정식

sulfuric acid

2-amino-4,5-ethylenedioxy-3',4'-dimethoxybenzophenone

ethyl 4-chloroacetoacetate

→

ethyl 2-chloromethyl-6,7-ethylenedioxy-4-(3,4-dimethoxyphenyl)quinoline-3-carboxylate

수율 60.1%

용매

acetic acid

반응 조건

후처리

1. 1
   농축The reaction mixture was concentrated under reduced pressure
2. 2
   workup.ADDITIONThe residue was poured into water
3. 3
   추출extracted with chloroform
4. 4
   세척The chloroform layer was washed with water
5. 5
   건조dried over magnesium sulfate
6. 6
   기타the solvent was evaporated under reduced pressure
7. 7
   세척The fractions eluted with chloroform-ethyl acetate (7:3

실험 절차

Conc. sulfuric acid (0.3 ml) was added to a mixture of 2-amino-4,5-ethylenedioxy-3',4'-dimethoxybenzophenone (6.5 g), ethyl 4-chloroacetoacetate (3.7 g) and acetic acid (60 ml), and the mixture was stirred at 100° C. for 3 hours. The reaction mixture was concentrated under reduced pressure. The residue was poured into water and made alkaline with 2N sodium hydroxide, and extracted with chloroform. The chloroform layer was washed with water and dried over magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was subjected to column chromatography on silica gel. The fractions eluted with chloroform-ethyl acetate (7:3, v/v) gave ethyl 2-chloromethyl-6,7-ethylenedioxy-4-(3,4-dimethoxyphenyl)quinoline-3-carboxylate (5.5 g, 60%). This compound was recrystallized from acetone. Colorless prisms, mp. 197°-198° C.

출처