반응 #3202

반응 방정식

methyl 2-amino-6-methylbenzoate

dimethyl acetylenedicarboxylate

potassium t-butoxide

→

title compound

수율 66.4%

Dimethyl 4-hydroxy-5-methylquinoline-2,3-dicarboxylate

수율 66.4%

용매

t-butanol

반응 조건

후처리

1. 1
   온도was refluxed fpr 18 hr under a nitrogen atmosphere
2. 2
   기타formed
3. 3
   온도After refluxing this mixture for 1.5 hr
4. 4
   온도it was cooled to room temperature
5. 5
   여과filtered
6. 6
   기타to separate the solids
7. 7
   workup.DISSOLUTIONThe solids were dissolved in water
8. 8
   기타to form a precipitate
9. 9
   여과The mixture was filtered
10. 10
    세척the collected solids were washed with water
11. 11
    기타dried

실험 절차

A stirred mixture of methyl 2-amino-6-methylbenzoate (1.50 g, 9.08 mM) and dimethyl acetylenedicarboxylate (1.40 g, 9.82 mM) in t-butanol (20 mL) was refluxed fpr 18 hr under a nitrogen atmosphere. The reaction mixture was cooled to room temperature and potassium t-butoxide (1.10 g, 9.82 mM) was added in one portion whereupon a precipitate formed. After refluxing this mixture for 1.5 hr, it was cooled to room temperature and filtered to separate the solids. The solids were dissolved in water and the resulting solution acidified with 1N H2SO4 to form a precipitate. The mixture was filtered and the collected solids were washed with water and dried to give the title compound (1.66 g, 66.4%) as a tan solid. An analytical sample of this material was obtained by recrystallization of a portion from ethyl acetate/hexane to give off white crystals, mp 167°-168° C.; MS(CI): 276 (M+H).

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