2-AMINO-5-HYDROXYBENZALDEHYDE synthesis

Yield:-

Reaction Conditions:

with hydrogen;palladium 10% on activated carbon in ethyl acetate at 15 - 20; under 760.051 Torr; for 5.5 h;

Steps:

1 Example 1 Synthesis of Compound (9)

To a solution of Compound (13) (1.7 g, 10 mmol) in ethyl acetate (17mL) was added 10% Pd-C (50% wet) (0.25 g) and hydrogenated for 5.5 hours at 15 to 20 °C at atmospheric pressure. The catalyst was filtered off and washed with ethyl acetate (8 mL). To thus-obtained solution of Compound (14) in ethyl acetate, an aqueous solution (33 mL) of sodium acetate (0.8 g) and acetic acid (3.3 mL) were added (pH 3.90) under ice-cooling. 3-methoxycarbonyl acrylate chloride (1.5 g) was added dropwise to the mixture under ice-cooling and the mixture was stirred for 50 minutes. The appeared crystals were collected by filtration, washed with water (20 mL) and ethyl acetate (5 mL) and dried to obtain 1.8 g of Compound (9) (yield: 72%).

References:

EP1489091,2004,A1 Location in patent:Page 11