반응 #217921

반응 방정식

dimethylformamide

6-chloronicotinamide

4-hydroxybenzaldehyde

potassium carbonate

→

title compound

수율 46.0%

6-(4-Formyl-phenoxy)-nicotinamide

수율 46.0%

용매

water

반응 조건

후처리

1. 1
   추출extract with diethyl ether (4×100 mL) and dichloroethane (2×100 mL)
2. 2
   건조Combine the organics, and dry over magnesium sulfate
3. 3
   여과Filter
4. 4
   농축concentrate in vacuo
5. 5
   기타purify by Biotage Flash 40L (elute with 50:50 hexanes/ethyl acetate to 100% ethyl acetate)

실험 절차

Combine 6-chloronicotinamide (4.53 g, 28.9 mmol), 4-hydroxybenzaldehyde (3.5 g, 28.9 mmol), potassium carbonate (6 g, 43.4 mmol), and dimethylformamide (200 mL). Heat the reaction mixture to 130° C. under nitrogen, and stir for 18 h. Dilute the reaction mixture with 200 mL of water, extract with diethyl ether (4×100 mL) and dichloroethane (2×100 mL). Combine the organics, and dry over magnesium sulfate. Filter, and concentrate in vacuo. Adsorb the residue on silica, and purify by Biotage Flash 40L (elute with 50:50 hexanes/ethyl acetate to 100% ethyl acetate) to afford the title compound as a white solid (3.2 g, 46%): 1H NMR (DMSO-d6): 10.0 (s, 1H), 8.59 (d, 1H), 8.26-8.22 (dd, 1H), 7.98-7.95 (m, 2H), 7.10-7.07 (d, 1H), 6.15-5.65 (br m, 2H).

출처