反応 #3211

反応方程式

methyl 2-amino-6-methoxybenzoate

dimethyl acetylenedicarboxylate

potassium t-butoxide

→

desired compound

収率 65.0%

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

収率 65.0%

溶媒

t-butanol

反応条件

後処理

1. 1
   温度the resulting mixture was heated to 90° C. for 1.5 hr during which solids
2. 2
   その他precipitated out of solution
3. 3
   温度The mixture was cooled to room temperature
4. 4
   ろ過filtered
5. 5
   workup.DISSOLUTIONthe collected solids were dissolved in water
6. 6
   その他to form a light tan precipitate
7. 7
   その他The solids were collected
8. 8
   ろ過filtered
9. 9
   洗浄washed with water and air
10. 10
    その他dried

実験手順

A solution of methyl 2-amino-6-methoxybenzoate ((1.30 g, 7.17 mM) and dimethyl acetylenedicarboxylate (1.17 g, 8.23 mM) in t-butanol (11 mL) was refluxed under a nitrogen atmosphere for 4 hr. The reaction mixture was cooled to room temperature, potassium t-butoxide (0.92 g, 8.23 mM) was added, and the resulting mixture was heated to 90° C. for 1.5 hr during which solids precipitated out of solution. The mixture was cooled to room temperature, filtered and the collected solids were dissolved in water. The resulting solution was acidified with 1N H2SO4 to form a light tan precipitate. The solids were collected, filtered, washed with water and air dried to provide the desired compound (1.35 g, 65%) as a tan solid. A 0.28 g portion of this material was recrystallized from ethyl acetate to provide an analytical sample (0.24 g) of the title compound as a white solid, mp 184°-186° C.; MS(CI): 292 (M+H).

出典