Triethylamine → HCID 23497814, compound

Participants

Reaction Conditions

Reaction Steps

5,5,8,8-Tetramethyl-5,6,7,8-tetrahydro-naphthalene-2-carboxylic acid 2 (1.38 g, 5.94 mmol) was dissolved in SOCl2 and two drops of DMF were added at 0° C. The mixture was stirred at 0° C. for 30 min and it was evaporated and this crude product was dissolved in CH2Cl2 (5 mL). B) 4-iodophenylamine (1.30 g, 5.94 mmol) and DMAP (73 mg, 0.59 mmol) were dissolved in CH2Cl2 (10 mL) and Et3N (8.4 mL) was added at 0° C. The Mixture A) was added in B) at 0° C. via syringe and the resulting mixture was stirred at 0° C. for 10 min and abandoned at RT for 2.5 h. A solution of aqueous NH4Cl 5% (50 mL) was added and the resulting mixture was extracted with EtOAc (3×150 mL). The organic layer was washed with NaHCO3 (2×100 mL) and brine (3×100 mL) and dried with MgSO4, filtered and evaporated. The crude product was purified by column chromatography using as eluent cyclohexane:EtOAc=90:10. 5,6,7,8-Tetrahydro-N-(4-iodophenyl)-5,5,8,8-tetramethylnaphthalene-2-carboxamide 22 was obtained (1.43 g, 56% yield) as a white solid.

Provenance & Evidence