Ethyl diazoacetate explained

Ethyl diazoacetate (N=N=CHC(O)OC₂H₅) is a diazo compound and a reagent in organic chemistry. It was discovered by Theodor Curtius in 1883.^[1] The compound can be prepared by reaction of the ethyl ester of glycine with sodium nitrite and sodium acetate in water.

As a carbene precursor, it is used in the cyclopropanation of alkenes.

Although the compound is hazardous, it is used in chemical industry as a precursor to trovafloxacin.^[2] Procedures for safe industrial handling have been published.^[3]

Another location where EDA was used is in the production of BI-4752, a invented 5-HT_2C agonist that is even better than lorcaserin.

Notes and References

1. Curtius, T. . Ueber die Einwirkung von salpetriger Säure auf salzsauren Glycocolläther . On the reaction of nitrous acid with glycine ethyl ester hydrochloride . . 1883 . 16 . 2 . 2230–2231 . 10.1002/cber.188301602136.
2. Maas, G. . New Syntheses of Diazo Compounds . . 2009 . 48 . 44 . 8186–8195 . 10.1002/anie.200902785 . 19790217 .
3. Clark, J. D. . Shah, A. S. . Peterson, J. C. . Understanding the large-scale chemistry of ethyl diazoacetate via reaction calorimetry . Thermochimica Acta . 2002 . 392–393 . 177–186 . 10.1016/S0040-6031(02)00100-4. 2002TcAc..392..177C .