N-Formyl-1-naphthylamine synthesis

Yield:6330-51-4 98%

Reaction Conditions:

with 2-methyl-1-butylimidazolium trifluoroacetate in neat (no solvent) at 70; for 2 h;

Steps:

General experimental procedure

General procedure: To a magnetically stirred mixture of HCO₂H (0.76 g, 14 mmol, 85%) and IL-III (126 mg, 0.5 mmol) was added N-allyl-N-benzyl amine (1.470 g, 10 mmol, Table 2, entry 6) and then the reaction mixture was heated in an oil bath at 70 °C. The progress of the reaction was monitored by TLC. After completion of reaction, the mixture was diluted with water (10 ml) and extracted with ether (10 ml ×3). The combined organic layer was washed with brine, dried over anhydrous Na₂SO₄ and evaporated to give residue under reduced pressure. The crude product was passed through a short pad silica-gel column (in order to remove any trace amount of ionic liquid left in the product) by elution with diethyl ether. The evaporation of the solvent under reduced pressure, dried under high vacuum afforded light yellowish sticky solid. The identity of the products was confirmed by IR, ¹H, ¹³C NMR and mass spectroscopy.

References:

Majumdar, Swapan;De, Jhinuk;Hossain, Jewel;Basak, Ajoy [Tetrahedron Letters,2013,vol. 54,# 3,p. 262 - 266]