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Nsc21429 synthesis

7synthesis methods
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Yield:5296-86-6 98%

Reaction Conditions:

Stage #1: 4-chlorophenylhydrazine hydrochloride in ethanol at 50; for 1 h;Inert atmosphere;
Stage #2: 2-oxo-propionic acid ethyl ester in ethanol at 20 - 50; for 4 h;Inert atmosphere;

Steps:

2-[(4-Chlorophenyl)-hydrazono]-propionic acid ethyl ester (HI).

A mixture of P-chlorophenyl hydrazine hydrochloride (2 g, 11.17 mmol, 1 equiv) in ethanol (15 mL) was stirred at 50 oC for 1 h under N2 atmosphere before addition of ethyl pyruvate (1.25 mL, 1.01 equiv). The resulting reaction mixture was stirred for further 5 min at 50 oC then at rt for 4h. The solvent was removed under reduced pressure to give HI (2.5g, 98%) as white solid and mixture of E and Z isomers.

References:

Mohamed, Fatma A.M.;Gomaa, Hesham A.M.;Hendawy;Ali, Asmaa T.;Farghaly, Hatem S.;Gouda, Ahmed M.;Abdelazeem, Ahmed H.;Abdelrahman, Mostafa H.;Trembleau, Laurent;Youssif, Bahaa G.M. [Bioorganic Chemistry,2021,vol. 112,art. no. 104960] Location in patent:supporting information