Hydrazine hydrate (1:1) → (3-Amino-4-hydroxyphenyl)acetic acid

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Reaction Conditions

Reaction Steps

Compound III was synthesized according to the method of Zupancic and Trpin J. Prac. Chem. 33, 307-308 (1966); CA 66, 37580c. To a stirred solution of sodium hydroxide solution (1 g in 40 ml) in a round bottom flask was added 3-nitro-4-hydroxyphenylacetic acid (4.93 g, 0.025 mol). The solid dissolved at once giving an orange color solution. 10% Pd—C (50 mg) was added followed by dropwise addition of hydrazine monohydrate (3.25 ml). After the completion of the addition (5 minutes), the mixture was heated at 60° C. for 1.5 hr. The temperature was raise to reflux and heating continued for additional 0.5 hr. The solution appeared clear with Pd—C suspended in it. The solution was filtered hot, concentrated to half of the volume and then cooled. The solution was acidified carefully to pH 4-5 with acetic acid. The white precipitate separated after cooling was filtered off and washed with ethanol. m.p. 225-227° C. lit2. 229-230° C. (3.4 g, yield 30%). 1H NMR(D2O, δ) 7.9 (1H, d, j=7 Hz, 6-H); 7.8 (s, 1H, 2-H); 7.65 (1H, d, J=7 Hz, 5-H); 3.4 (2H, s, CH2COOH).

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