반응 #8997

반응 방정식

Terephthaldicarboxaldehyde

2-(aminomethyl)pyridine

hydrogen

→

title compound

수율 78.0%

4-hydroxymethylbenzaldehyde

수율 78.0%

용매

methanol

반응 조건

후처리

1. 1
   여과The mixture was filtered through celite
2. 2
   세척the cake washed with methanol
3. 3
   기타the solvent from the eluent removed in vacuo
4. 4
   기타Purification of the crude product by column chromatography on silica gel (EtOAc/Hexanes, 1:1)

실험 절차

Terephthaldicarboxaldehyde (30.02 g, 224 mmol), methanol (200 mL), palladium on activated carbon, (10%, 3.02 g) and 2-(aminomethyl)pyridine (2.3 mL, 22 mol, 0.01 mol equiv) were combined in a hydrogenation vessel and the reaction mixture was shaken on a Parr hydrogenator for 2.5 hours at 40 psi of hydrogen. The mixture was filtered through celite, the cake washed with methanol and the solvent from the eluent removed in vacuo. Purification of the crude product by column chromatography on silica gel (EtOAc/Hexanes, 1:1) afforded the title compound (23.8 g, 78%) as a white solid. 1H NMR (CDCl3) δ 4.80 (s, 2H), 7.53 (d, 2H, J=9 Hz), 7.87 (d, 2H, J=9 Hz), 10.00 (s, 1H).

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