تفاعل #84209

معادلة التفاعل

MeMgBr

2-Methylindole

3-(1-naphthoyl)-1H-indole

1-naphthoic acid

→

(2-methyl-1H-indol-3-yl)(naphthalen-1-yl) methanone

المذيبات

diethylether

thionyl chloride

ظروف التفاعل

المعالجة

1. 1
   درجة الحرارةrefluxed for 90 min
2. 2
   أخرىthe solvent was removed under vacuo
3. 3
   workup.DISSOLUTIONthe residue was dissolved in diethylether (50 ml)
4. 4
   workup.ADDITIONThe resulting solution was added dropwise to the indole reaction mixture at 0° C.
5. 5
   workup.STIRRINGto stir at room temperature for 2 hours
6. 6
   workup.ADDITIONA solution of ammonium chloride (200 ml) was added to the reaction mixture
7. 7
   workup.STIRRINGthe resulting mixture was stirred at room temperature overnight
8. 8
   أخرىThe solid that was formed
9. 9
   ترشيحwas collected by filtration
10. 10
    غسيلwashed with water and hexane
11. 11
    تجفيفthen dried in a dessicator over phosphorous pentoxide

الإجراء التجريبي

2-Methylindole 1 (10 g, 76 3 mmol) was dissolved in diethylether (100 ml) under nitrogen atmosphere and cooled to 0° C. MeMgBr (3M) solution (26.7 ml, 80.15 mmol) was added dropwise and allowed to stir at room temperature for 3 hours. In the meantime, 1-naphthoic acid (13.13 g, 76 3 mmol) was dissolved in thionyl chloride (50 ml) and refluxed for 90 min, then the solvent was removed under vacuo and the residue was dissolved in diethylether (50 ml). The resulting solution was added dropwise to the indole reaction mixture at 0° C. and then allowed to stir at room temperature for 2 hours. A solution of ammonium chloride (200 ml) was added to the reaction mixture and the resulting mixture was stirred at room temperature overnight. The solid that was formed was collected by filtration, washed with water and hexane then dried in a dessicator over phosphorous pentoxide to give 9.7 g (45%) (2-methyl-1H-indol-3-yl)(naphthalen-1-yl) methanone 2 as a cream solid.

المصدر