반응 #2269997

반응 방정식

(4-chlorophenyl)(1-methyl-1H-pyrrol-2-yl)methanone

isonicotinoyl chloride

aluminum chloride

→

title compound

수율 27.0%

[5-(4-Chlorobenzoyl)-1-methyl-1H-pyrrol-3-yl]pyridin-4-ylmethanone

수율 27.0%

용매

DCE

반응 조건

후처리

1. 1
   온도under reflux for 16 h
2. 2
   온도After cooling
3. 3
   기타the mixture was partitioned between CH2Cl2 and dilute NaOH solution
4. 4
   기타The organic layer was dried
5. 5
   기타the solvent was evaporated in vacuo
6. 6
   기타The residue was triturated with ether
7. 7
   기타The resulting solid was recrystallized from 2-PrOH

실험 절차

A solution of 17.5 g (0.08 mole) of (4-chlorophenyl)(1-methyl-1H-pyrrol-2-yl)methanone, 14.4 g (0.088 mole) of isonicotinoyl chloride and 26.6 g of aluminum chloride (0.2 mole) in 280 mL of DCE was heated under reflux for 16 h. After cooling, the mixture was partitioned between CH2Cl2 and dilute NaOH solution. The organic layer was dried and the solvent was evaporated in vacuo. The residue was triturated with ether. The resulting solid was recrystallized from 2-PrOH to give 7 g (27%) of the title compound, mp 174-175° C. ES-MS m/z=325 (M++H). 1H NMR (300 MHz, CDCl3) δ 4.1 (s, 3H); 7.1 (s, 1H); 7.3(dd, 2H); 7.42 (dd, 2H); 7.45 (s, 1H); 7.8 (dd, 2H); 8.8 (dd, 2H). Anal calc'd for: C18H13ClN2O2: C, 66.57; H, 4.03; N, 8.63. Found: C, 66.34; H, 3.94; N, 8.53.

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