Dimethylamine → HCID 71186206, compound

Participants

Reaction Steps

To a mixture of 8-chloro-4-methoxy-1-naphthoic acid (step-4 intermediate) (0.5 g, 2.11 mmol) in CH2Cl2 (5 mL) was added, SOCl2 (0.31 mL, 4.22 mmol, 2.0 eq.) and the mixture was stirred at RT for 3 h. The solvent was evaporated under reduced pressure and the crude product was dissolved in DCM (10 mL). To this, DIPEA (0.74 mL, 4.23 mmol) was added followed by dimethylamine (1.5 eq.) and the reaction mixture was stirred at RT for 3 h and then quenched with ice. The aqueous layer was extracted with dichloromethane and the combined organic layer was washed with sat. NaHCO3 solution, water, brine, dried over Na2SO4 and filtered. The solvent was evaporated to provide the desired amide derivative (528 mg, 95%) this was used in the next step without any further purification.

Provenance & Evidence