Synthesis
Preparative Example 5: Synthesis of 2-methoxyacetohydrazide
Hydrazine monohydrate (9.85 mL, 202 mmol) was slowly added to a solution of methyl methoxyacetate (10 mL, 101 mmol) in methanol (50 mL). The reaction mixture was continuously stirred and heated at 70 °C for 18 hours. Upon completion of the reaction, the mixture was cooled to room temperature and subsequently concentrated under reduced pressure in a rotary evaporator to remove the solvent. Toluene (2 x 50 mL) was added to the residue for azeotropic dehydration to give a white solid product. The solid was ground with ether (50 mL) for further purification, followed by vacuum drying at 50 °C for 30 min to give the final methoxyacetylhydrazine as a white solid in 95% yield (9.98 g). The product was characterized by 1H NMR (400 MHz, DMSO-d6): δ 3.26 (s, 3H), 3.79 (s, 2H), 4.22 (bs, 2H), 8.97 (bs, 1H).
References
[1] Bioorganic and Medicinal Chemistry Letters, 2010, vol. 20, # 2, p. 516 - 520
[2] Patent: US2006/160786, 2006, A1. Location in patent: Page/Page column 22
[3] Patent: WO2005/74904, 2005, A2. Location in patent: Page/Page column 57-58
[4] Patent: WO2004/108661, 2004, A1. Location in patent: Page/Page column 51
[5] Patent: WO2005/63742, 2005, A2. Location in patent: Page/Page column 23
