反応 #3201

反応方程式

methyl 2-amino-4,6-dichlorobenzoate

dimethyl acetylenedicarboxylate

potassium t-butoxide

→

title compound

収率 59.0%

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

収率 59.0%

溶媒

t-butanol

反応条件

後処理

1. 1
   その他formed
2. 2
   温度After refluxing for 1.5 hr
3. 3
   温度the reaction mixture was cooled to room temperature
4. 4
   ろ過filtered
5. 5
   その他to separate the precipitated solids
6. 6
   洗浄The solids were washed with t-butanol
7. 7
   workup.DISSOLUTIONdissolved in water
8. 8
   その他the resulting precipitate was collected
9. 9
   洗浄washed thoroughly with water
10. 10
    その他dried

実験手順

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).

出典