Acetic Acid → Dimethyl 5-(diethylamino)isophthalate

Participants

Reaction Steps

Acetaldehyde (1.07 ml, 0.8 g, 19.12 mmol, 8 eq) was added to a stirred solution of dimethyl 5-aminoisophthalate (0.500 g, 2.39 mmol, 1 eq) in CH3CN (15 ml) and water (0.5 ml) at 0° C. After 10 min NaBH3CN (0.395 g, 5.98 mmol, 2.5 eq) was added. The reaction was adjusted to pH {tilde over ( )} 7 with HOAc. After 1.5 h the reaction was adjusted to pH {tilde over ( )} 7 with HOAc a second time. The reaction was stirred at 0° C. to room temperature overnight. The solvent was removed in vacuo, and the residue was dissolved in EtOAc. The organic layer was washed with saturated aqueous NaHCO3 (×2), water (×3), brine (×1), and dried over Na2SO4. The inorganics were filtered off, and the solvent was removed in vacuo. Purification via flash chromatography yielded 0.575 g (2.17 mmol, 91% yield) of the product.

Provenance & Evidence