반응 #3201

반응 방정식

methyl 2-amino-4,6-dichlorobenzoate

dimethyl acetylenedicarboxylate

potassium t-butoxide

→

title compound

수율 59.0%

Dimethyl 5,7-dichloro-4-hydroxyquinoline-2,3-dicarboxylate

수율 59.0%

용매

t-butanol

반응 조건

후처리

1. 1
   기타formed
2. 2
   온도After refluxing for 1.5 hr
3. 3
   온도the reaction mixture was cooled to room temperature
4. 4
   여과filtered
5. 5
   기타to separate the precipitated solids
6. 6
   세척The solids were washed with t-butanol
7. 7
   workup.DISSOLUTIONdissolved in water
8. 8
   기타the resulting precipitate was collected
9. 9
   세척washed thoroughly with water
10. 10
    기타dried

실험 절차

A solution of methyl 2-amino-4,6-dichlorobenzoate (1.30 g, 5.91 mM) and dimethyl acetylenedicarboxylate (0.96 g, 6.78 mM) in t-butanol (14 mL) was refluxed for 18 hr under a nitrogen atmosphere. The reaction mixture was cooled to room temperature and potassium t-butoxide (0.76 g, 6.8 mM) was added to the stirred mixture whereupon a precipitate formed. After refluxing for 1.5 hr, the reaction mixture was cooled to room temperature and filtered to separate the precipitated solids. The solids were washed with t-butanol and then dissolved in water. The resulting solution was acidified with 1N H2SO4 and the resulting precipitate was collected, washed thoroughly with water and dried to give the title compound as a light green solid (1.15 g, 59%). An analytical sample was obtained by recrystallization of a portion from toluene to provide the title compound as a light tan solid, mp 109.5°-111° C. (d); MS(CI): 330 (M+H).

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