Uses
Formic acid hydrazide is used as a precursor in the preparation of 1,2,4-triazole derivatives. It is also used in the synthesis of 6-N-formylamino-12,13-dihydro-1,11-dihydroxy-13-(beta-D-glucopyranosyl)-5H-indolo[2,3-a]-pyrrolo[3,4-c]carbazole-5,7(6H)-dione, which is an anticancer agent.
Synthesis
a) Preparation of Formylhydrazine: Mix ethyl formate (200 g) with methanol (200 mL) and cool to 0-10°C. Under stirring, slowly add a mixed solution of hydrazine hydrate (138 g) and water (20 mL). The reaction mixture was gradually heated to 55-60°C and stirred continuously at this temperature for 24 hours. Upon completion of the reaction, the solvent was removed by distillation under reduced pressure. Isopropanol was added to the residue and the mixture was cooled to 0-5°C and stirred for 2 hours. The solid product was collected by filtration, washed with isopropanol and dried to give formylhydrazine. Yield: 140 g.
Purification Methods
Recrystallise it from EtOH and dry it in vacuo. Store below 10o; it may disproportionate on storage to 1,2-diformyl hydrazine and hydrazine. It forms a blue [Cu(CH4N2O)]SO4 salt with CuSO4. [Beilstein 2 H 93, 2 III 127, 2 IV 85.]
References
[1] Chemistry of Heterocyclic Compounds, 2006, vol. 42, # 2, p. 233 - 245
[2] Synthesis, 2006, # 9, p. 1504 - 1512
[3] Chemistry - An Asian Journal, 2012, vol. 7, # 4, p. 715 - 724
[4] Gazzetta Chimica Italiana, 1894, vol. 24 II, p. 225
[5] Journal of pharmaceutical sciences, 1970, vol. 59, # 1, p. 105 - 107
