반응 #1536745

반응 방정식

methyl 2-amino-6-methoxybenzoate

dimethyl acetylenedicarboxylate

potassium t-butoxide

→

desired compound

수율 65.0%

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

수율 65.0%

용매

t-butanol

반응 조건

후처리

1. 1
   workup.ADDITIONwas added
2. 2
   기타precipitated out of solution
3. 3
   온도The mixture was cooled to room temperature
4. 4
   여과filtered
5. 5
   workup.DISSOLUTIONthe collected solids were dissolved in water
6. 6
   기타to form a light tan precipitate
7. 7
   기타The solids were collected
8. 8
   여과filtered
9. 9
   세척washed with water and air
10. 10
    기타dried

실험 절차

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).

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