Triethylamine → HCID 14520026, compound

Participants

Reaction Steps

A solution of oxalyl chloride (0.95 mL, 11 mmol) in CH2Cl2 (10 mL) was added to a suspension of 2,6-dimethoxy-1-naphthalenecarboxylic acid (2.32 g, 10 mmol, described in Example 1) and N,N-dimethylformamide (2 drops, catalyst) in CH2Cl2 (50 mL) under nitrogen. After 1.5 hours, triethylamine (5 mL, 36 mmol) and N-methylglycine methyl ester hydrochloride (2.1 g, 15 mmol) were added. The resulting mixture was stirred at room temperature overnight and then poured into water (200 mL) and CH2Cl2 (200 mL). The aqueous phase was washed with CH2Cl2 (100 mL) and the combined CH2Cl2 phases were washed successively with 1M H3PO4 (2×100 mL), water (100 mL), saturated NaHCO3 (50 mL), brine (100 mL) and dried over Na2SO4. Filtration and concentration left a pale brown foam which was filtered through a short column of silica gel with 1:1 ethyl acetate:hexane to obtain 2.53 g of the title compound as a pale yellow oil.

Provenance & Evidence