Acetic Acid → 3-[(Furan-2-yl-methyl)-amino]-phthalic acid dimethyl ester

Participants

Reaction Steps

To a stirred solution of 3-amino-phthalic acid dimethyl ester (8.23 g, 39.32 mmol) in methylene chloride (200 ml) under a nitrogen atmosphere, 2-furaldehyde (8.14 ml, 98.30 mmol) and acetic acid (13.57 ml, 235.92 mmol) were added. The mixture was stirred for 5 minutes, followed by addition of sodium triacetoxyborohydride (25 g, 117.96 mmol). The reaction was stirred overnight, washed with water (2×200 ml), saturated aqueous sodium bicarbonate (2×200 ml), and brine (200 ml), and dried over MgSO4. The solvent was evaporated in vacuo to give a brown oil (12.42 g), which was used directly without purification.

Provenance & Evidence