反応 #3202

反応方程式

methyl 2-amino-6-methylbenzoate

dimethyl acetylenedicarboxylate

potassium t-butoxide

→

title compound

収率 66.4%

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

収率 66.4%

溶媒

t-butanol

反応条件

後処理

1. 1
   温度was refluxed fpr 18 hr under a nitrogen atmosphere
2. 2
   その他formed
3. 3
   温度After refluxing this mixture for 1.5 hr
4. 4
   温度it was cooled to room temperature
5. 5
   ろ過filtered
6. 6
   その他to separate the solids
7. 7
   workup.DISSOLUTIONThe solids were dissolved in water
8. 8
   その他to form a precipitate
9. 9
   ろ過The mixture was filtered
10. 10
    洗浄the collected solids were washed with water
11. 11
    その他dried

実験手順

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).

出典