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3-(DIMETHYLAMINO)BENZOHYDRAZIDE synthesis

4synthesis methods
3-Dimethylaminobenzoic acid ethyl ester

16518-65-3
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3-(DIMETHYLAMINO)BENZOHYDRAZIDE

205927-64-6
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Yield:205927-64-6 1.02 g

Reaction Conditions:

with hydrazine hydrate in ethanol;Reflux;

Steps:

Compound 44a.

To a solution of 3-(dimethylamino)benzoic acid (1 g, 6.05 mmol) in ethanol (10 mL) was added cHCl (5 drops) and the mixture heated at reflux overnight. The solvents were evaporated to give the target compound as a white solid. This compound was then dissolved in ethanol (10 mL) and hydrazine hydrate (5.89 mL, 121 mmol) was added and the mixture heated at reflux overnight. Solvents were evaporated and the product was purified by flash chromatography using a gradient mixture of ethyl acetate and hexanes to give the desire compound as a white solid (1.02 g, 93% over 2 steps). 1H NMR (CDCl3), δ 2.95 (s, 6H), 6.84 (d, J = 8 Hz, 1H), 6.99 (d, J = 7 Hz, 1H), 7.19 (m, J = 20 Hz, 1H), 7.26 (m, J = 6 Hz, 1H); MS m/z = 180.6 (M + H)+.

References:

Goodman, Allan;McCall, Jennifer R.;Jacocks, Henry M.;Thompson, Alysha;Baden, Daniel;Abraham, William M.;Bourdelais, Andrea [Marine Drugs,2014,vol. 12,# 4,p. 1839 - 1858]

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