تفاعل #216052

معادلة التفاعل

sodium hydroxide

compound K

Methyl 1-(2-chlorobenzoyl)-3-(2-chlorophenyl)-5,7-dimethylindole-2-carboxylate

HCl

→

methyl 3-(2-chlorophenyl)-1,5,7-trimethylindole-2-carboxylate

المردود 58.9%

المذيبات

methanol

ظروف التفاعل

المعالجة

1. 1
   workup.ADDITIONby adding
2. 2
   درجة الحرارةunder reflux for 2 hours
3. 3
   درجة الحرارةAfter cooling
4. 4
   استخلاصfollowed by extraction with ethyl acetate
5. 5
   تجفيفThe extract was dried over magnesium sulfate
6. 6
   workup.DISTILLATIONdistilled
7. 7
   أخرىto remove the solvent
8. 8
   workup.DISSOLUTIONThe resulting crude product was dissolved in 2 cc of dimethylformamide
9. 9
   workup.ADDITION0.26 g of 63% sodium hydride in 1.5 cc of dimethylformamide was added at room temperature
10. 10
    workup.ADDITION0.4 cc of methyl iodide was added dropwise
11. 11
    workup.STIRRINGstirred for 2 hours
12. 12
    workup.ADDITIONWater was added to the reaction mixture
13. 13
    استخلاصfollowed by extraction with ethyl acetate
14. 14
    تجفيفThe extract was dried over magnesium sulfate
15. 15
    workup.DISTILLATIONdistilled
16. 16
    أخرىto remove the solvent
17. 17
    أخرىThe crude product thus obtained
18. 18
    غسيلwas washed with hexane

الإجراء التجريبي

Methyl 1-(2-chlorobenzoyl)-3-(2-chlorophenyl)-5,7-dimethylindole-2-carboxylate (compound K) was obtained in the same manner as for compounds I and J in Reference Example 4. In 20 cc of methanol was dissolved 0.96 g of compound K, followed by adding thereto 4.2 cc of 2N sodium hydroxide, and the resulting mixture was heated under reflux for 2 hours. After cooling, the mixture was acidified with 2N HCl, followed by extraction with ethyl acetate. The extract was dried over magnesium sulfate and distilled to remove the solvent. The resulting crude product was dissolved in 2 cc of dimethylformamide, and 0.26 g of 63% sodium hydride in 1.5 cc of dimethylformamide was added at room temperature. The resulting mixture was stirred at room temperature for 30 minutes, and then 0.4 cc of methyl iodide was added dropwise and stirred for 2 hours. Water was added to the reaction mixture, followed by extraction with ethyl acetate. The extract was dried over magnesium sulfate and distilled to remove the solvent. The crude product thus obtained was washed with hexane to obtain 0.41 g of methyl 3-(2-chlorophenyl)-1,5,7-trimethylindole-2-carboxylate (compound L).

المصدر